Water → HCID 68089123, compound

HRID 1631877Notes

Reaction equation

HRID 1631877 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12](/[CH:15]=[C:16]2/[C:17](=[O:31])[CH:18]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])[C:19](=[O:21])[CH2:20]/2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32](Cl)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34].O>ClCCl.C(N(CC)CC)C>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12](/[CH:15]=[C:16]2/[C:17](=[O:31])[CH:18]([C:22]3[C:23]([CH3:30])=[CH:24][C:25]([CH3:29])=[CH:26][C:27]=3[CH3:28])[CH:19]([O:21][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:20]/2)[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 66868058HCID 66868058, compound

Product 1

HCID 68089123HCID 68089123, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of the 4-[1-(4-benzyloxy-cyclohexyl)-meth-(E)-ylidene]-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (4.0 g, 9.6 mmol) in dichloromethane (60 ml) and triethylamine (2 ml) is added the pivaloyl chloride (1.73 g, 14.3 mmol) at 0° C. The reaction is allowed to warm to room temperature and then stirred for 3 hours. The reaction mixture is poured into water (50 ml) and extracted with dichloromethane (2×50 ml). The combined organic extracts are dried over magnesium sulphate, filtered and evaporated to give 2,2-dimethyl-propionic acid 4-[1-(4-benzyloxy-cyclohexyl)-meth-(E)-ylidene]-3-oxo-2-(2,4,6-trimethyl-phenyl)-cyclopentyl ester (4.5 g).

Workup

  1. extractionextracted with dichloromethane (2×50 ml)
  2. dry with materialThe combined organic extracts are dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-99b6057b7322488c9d0002b96f105161
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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