Salicylaldehyde → Methyl (7E)-8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxo-7-octenoate

HRID 2243294Notes

Reaction equation

HRID 2243294 reaction equation
C(OP([CH2:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])(OCC)=O)C.[H-].[Na+].[CH:22]1([C:28]2[CH:43]=[CH:42][C:31]([CH2:32][O:33][C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=3[CH:36]=O)=[CH:30][CH:29]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)C1C(=CC=CC=1)O.C1(C2C=CC(CCl)=CC=2)CCCCC1>C1COCC1.O>[CH:22]1([C:28]2[CH:43]=[CH:42][C:31]([CH2:32][O:33][C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=3/[CH:36]=[CH:9]/[C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:30][CH:29]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

8

Reactant 5

HCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 133433651-(Chloromethyl)-4-cyclohexylbenzeneHCID 15546840Methyl 7-(diethoxyphosphoryl)-6-oxoheptanoateHCID 866188632-[(4-Cyclohexylbenzyl)oxy]benzaldehyde

Product 1

HCID 59210853Methyl (7E)-8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxo-7-octenoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Under argon, a solution of 3.00 g (10.19 mmol) of methyl 7-(diethoxyphosphoryl)-6-oxo-heptanoate XIIb in 10 ml of THF was added dropwise to a suspension of 0.25 g (10.19 mmol) of sodium hydride in 20 ml of THF. After 30 min, a solution of 2.50 g (8.49 mmol) of 2-[(4-cyclohexylbenzyl)oxy]benzaldehyde (obtainable from salicylaldehyde and 4-cyclohexylbenzyl chloride in 10 ml of THF was added dropwise. The mixture was stirred at room temperature for 2 days. Water was added, the mixture was extracted with ethyl acetate and the combined organic phases were dried over Na2SO4. The product was purified chromatographically (silica gel, cyclo-hexane/ethyl acetate 10:1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over Na2SO4
  3. customThe product was purified chromatographically (silica gel, cyclo-hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-67864c13a26042e8b6d29eff7593f2a5
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

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