The Preparation of Benzyloxyalkyl p-Toluenesulfonates

A Highly Convergent Approach toward (−)-Brevenal

“…The synthesis commenced with a monobenzylation of commercially available 1,4-butanediol10 ( 13 ) followed by a Jones’ oxidation11 to afford carboxylic acid 14 (Scheme 3). Conversion to the methyl ester under acidic conditions followed by displacement with lithiodimethyl methylphosphonate12 then furnished β-ketophosphonate 12 in excellent yield over the four steps.…”

Synthesis and spectroscopic characterisation of non‐aggregated novel axially 4‐{2‐[3‐(diethylamino)phenoxy]ethoxy} and crown ether substituted silicon phthalocyanines

“…The synthetic route of the compounds presented in this work is shown in Figure 1. Compounds dichloro(phthalocyaninato) silicon 1 [29], 2‐[3‐(diethylamino) phenoxy]ethanol 2 [30], 2‐hydroxymethyl(12‐crown‐4) 4 [31] and 2‐hydroxymethyl(18‐crown‐6) 6 [32] were synthesised according to previously published methods. Axially substituted silicon phthalo‐cyanines 3 , 5 and 7 were synthesised from silicon phthalocyanine dichloride 1 .…”

“…Silicon phthalocyanine dichloride 1 [29], 2‐[3‐(diethy‐lamino)phenoxy]ethanol 2 [30], 2‐hydroxymethyl(12‐crown‐4) 4 [31] and 2‐hydroxymethyl(18‐crown‐6) 6 [32] were prepared according to the literature. All reagents and solvents were of reagent grade quality and were obtained from commercial suppliers.…”

Concave reagents. 12. Polymerfixation of Concave Pyridines

“…During 5min, 6.90g (288mmol) of NaH which had been washed with dry petroleum ether (b. p. 30 -50 "C) was added to 200 g (1.32 mol) of 2-benzyloxyethanol [6] which was stirred and cooled by ice. Then slowly 5.0g (29mmol) of 4chloropyridine-2,6-dimethanol (1) [3] was added to the orange reaction mixture.…”

“…To isolate the product, ca. 150g of the solvent was distilled off at 15 Torr, the mixture was cooled to room temp., diluted with 100ml of water, cooled (6) Under nitrogen 420 mg (2.8 mmol) of 3,6-dioxaoctan-l,8diamine (4) was added to a stirred solution of 800mg (2.8 mmol) of 4-(2-benzyloxyethoxy)-pyridine-2,6-dicarbaldehyde (3) and 570mg (2.8mmol) of MgC12 . 6H20 in 50ml of dry methanol.…”