HCID 68637842, compound → HCID 86595374, compound
Reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH2:12]([O:19][CH:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:12]([O:19][CH:20]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[O:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
PCC (9.7 g, 45 mmol) was added in portions to a solution containing 6-benzyloxy-1-tetradecanol (7.5 g, 30 mmol) in methylene chloride (100 ml) at RT. The black mixture was stirred for 2 hours, then filtered through a bed of silica gel using hexane:ethyl acetate (90:10). The corresponding aldehyde, 6-benzyloxy-tetradecanal, was produced at a yield of 6.1 g (81%). This aldehyde compound was mixed with carbethoxymethylene triphenylphosphorane (10 g, 29 mmol) in 100 ml of methylene chloride at RT. The mixture was allowed to stir overnight, after which the solvent was removed and replaced with hexane. Solid precipitates were removed by filtration. Following chromatography on silica gel using hexane:ethyl acetate at a ratio of 90:10, the corresponding ester was detected at 8.4 g scale (90%). The chemical shift of the ester, 8-benzyloxyhexadec-2-enoate ethyl ester, is as follows: 1H-NMR (CDCl3) δ 0.89 (m, 6H, CH3), 1.2-1.5 (m, 20H, CH2), 2.2 (m, 2H, CH2—C═), 3.35 (m, 2H, CH2O), 4.2 (q, 2H, MeCH2—O), 4.55 (dd, 2H, CH2—O), 5.8 (d, 1H, CH═C), 6.95 (d, t 1H, CH═C), 7.35 (m, 5H, benzyl).
Workup
- filtrationfiltered through a bed of silica gel
Sources & evidence
- ORD record
- ord-94f342d2913c4b178540cf908dd6d791
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08309053B2
Reaction notes
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