Water → HCID 21397385, compound

HRID 1439485Notes

Reaction equation

HRID 1439485 reaction equation
[H-].[Na+].[C:3]1([CH:9]([CH2:13][CH2:14][CH2:15][CH:16]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:10](=[O:12])[CH3:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].O>C1C=CC=CC=1.CN(C)C=O.CCOCC>[C:10]([C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([CH2:13][CH2:14][CH2:15][CH:16]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])(=[O:12])[CH3:11]

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 213973967-(Benzyloxy)-3-phenyldodecan-2-one

Product 1

HCID 21397385HCID 21397385, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.8 g., 0.033 mole) is suspended in a mixture of benzene (50 ml.) and dimethylformamide (50 ml.) and 3-phenyl-7-benzyloxy-2-dodecanone (12.1 g., 0.033 mole) is added dropwise. The resulting mixture is heated on the steam bath for one hour and then cooled to room temperature. Ethyl 7-bromoheptanoate (8.8 g., 0.037 mole) is added dropwise and the mixture is heated on the steam bath for 24 hours. The reaction mixture is cooled, poured into water (200 ml.) and the oily product taken up into ether and dried over sodium sulfate. The solvent is distilled in vacuo to leave 14 g. of ethyl 8-acetyl-8-phenyl-12-benzyloxyheptadecanoate as a yellow oil which is used in Step G without further purification.

Workup

  1. additionis added dropwise
  2. temperatureThe resulting mixture is heated on the steam bath for one hour
  3. temperaturethe mixture is heated on the steam bath for 24 hours
  4. temperatureThe reaction mixture is cooled
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent is distilled in vacuo
  7. customto leave 14 g
  8. customof ethyl 8-acetyl-8-phenyl-12-benzyloxyheptadecanoate as a yellow oil which is used in Step G without further purification

Sources & evidence

ORD record
ord-d7c6813ddfbd4da783827837d3c4ec7f
Source dataset
uspto-grants-1977_11
Patent number
US04059602

Reaction notes

Loading…