Potassium Carbonate → Oxacycloheptadec-8-en-2-one, (8Z)-

HRID 1383287Notes

Reaction equation

HRID 1383287 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]>CN1CCCC1=O>[O:24]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1=[O:25]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 867570997Z-16-bromohexadec-7-enoic acid

Product 1

HCID 5365703Oxacycloheptadec-8-en-2-one, (8Z)-Yield 79.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

41 g of potassium carbonate were suspended in 600 ml of N-methyl-pyrrolidone. A solution of 51 g (0.15 mol) of 7Z-16-bromohexadec-7-enoic acid in 400 ml of N-methylpyrrolidone was added dropwise at 90° C. within 8 hours. After usual work up and chromatography 30 g (77%) of 8Z-oxacycloheptadec-8-en-2-one were obtained having the following characteristics: Z/E=90/10;

Sources & evidence

ORD record
ord-e351e90aac9c47899406a24de26ec717
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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