Triethylamine → HCID 178455063, compound

HRID 585681Notes

Reaction equation

HRID 585681 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[CH:11][C:10]=1[C@@H:23]1[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25][CH2:24]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>O.ClCCl>[CH3:46][S:47]([O:29][C@H:26]1[CH2:25][CH2:24][C@@H:23]([C:10]2[CH:11]=[CH:12][C:13]([O:15][Si:16]([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:18])[CH3:17])=[CH:14][C:9]=2[O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[CH2:28][CH2:27]1)(=[O:49])=[O:48]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 178455058HCID 178455058, compound

Product 1

HCID 178455063HCID 178455063, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask containing cis-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (200 mg, 0.46 mmol) was added dichloromethane (10 ml) followed by triethylamine (96 μl, 0.69 mmol) and dimethylaminopyridine (catalytic amount). The flask was purged with argon and methane sulfonyl chloride (53 μl, 0.69 mmol) was added with stirring. Stirring was continued for a further 24 hr and the reaction mixture was poured into water and extracted with dichloromethane (4×20 ml). The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo. Purification via flash column chromatography (SiO2, ethyl acetate/petrol, 1:9) afforded the title compound as an oil (194 mg, 82%). δH (CDCl3) 0.19 (6H, s), 0.22 (6H, s), 0.97 (9H, s), 1.01 (9H, s), 1.20-1.35 (2H, m), 1.65-1.78 (4H, m), 2.15-2.22 (2H, m), 2.85-2.95 (1H, m), 3.02 (3H, s), 5.06 (1H, s), 6.30 (1H, d), 6.43 (1H, dd), 7.00 (1H, d).

Workup

  1. additionwas added
  2. stirringStirring
  3. extractionextracted with dichloromethane (4×20 ml)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification via flash column chromatography (SiO2, ethyl acetate/petrol, 1:9)

Sources & evidence

ORD record
ord-5640cf5e214c42419063654e42381990
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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