HCID 68637842, compound → HCID 86595374, compound

HRID 539393Notes

Reaction equation

HRID 539393 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]=1

Participants

4

Reactant 2

HCID 68637842HCID 68637842, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86595374HCID 86595374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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-enoa- to ethyl ester, is as follows: .sup.1H-NMR (CDCl3).delta. 0.89 (m, 6H, CH3), 1.2-1.5 (m, 20H, CH2), 2.2 (m, 2H, CH2-C.dbd.), 3.35 (m, 2H, CH2O), 4.2 (q, 2H, MeCH2-O), 4.55 (dd, 2H, CH2-O), 5.8 (d, 1H, CH.dbd.C), 6.95 (d,t 1H, CH.dbd.C), 7.35 (m, 5H, benzyl).

Workup

  1. filtrationfiltered through a bed of silica gel

Sources & evidence

ORD record
ord-67695342f9554d5ca3bee6209b0db74b
Source dataset
uspto-grants-2014_10
Patent number
US08871179B2

Reaction notes

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