Triethylamine → HCID 178482824, compound

HRID 585676Notes

Reaction equation

HRID 585676 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:19])[C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1.[Si:20]([O:27][C:28]1[CH:33]=[C:32]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:31]=[CH:30][C:29]=1[C@H:42]1[CH2:47][CH2:46][C@H:45]([OH:48])[CH2:44][CH2:43]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:8][N:9]([CH3:19])[C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:48][C@H:45]2[CH2:46][CH2:47][C@H:42]([C:29]3[CH:30]=[CH:31][C:32]([O:34][Si:35]([C:38]([CH3:40])([CH3:41])[CH3:39])([CH3:37])[CH3:36])=[CH:33][C:28]=3[O:27][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[CH2:43][CH2:44]2)=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 44007824-(Dimethylamino)benzoyl chlorideHCID 178455059HCID 178455059, compound

Product 1

HCID 178482824HCID 178482824, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (20 μl), 4-dimethylaminopyridine (catalytic amount) and 4-dimethylaminobenzoyl chloride (26 mg) were added to a stirred solution of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (30 mg) in dry dichloromethane (2 ml) at room temperature under argon. After 24 hr, the solvent was removed under reduced pressure and the residue was partitioned between water (10 ml) and ethyl acetate (20 ml). The aqueous layer was extracted with ethyl acetate (2×20 ml) and the combined organic extracts were washed with brine (10 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:24 v/v) to give the title compound as a white solid (18 mg, 45%); m/z (ES+) 585 (M+H)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water (10 ml) and ethyl acetate (20 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×20 ml)
  4. washthe combined organic extracts were washed with brine (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:24 v/v)

Sources & evidence

ORD record
ord-30a00887ea794c8094c79ba0b955bf80
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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