Phenyl isocyanate → HCID 178455061, compound

HRID 1007965Notes

Reaction equation

HRID 1007965 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]1([N:16]=[C:17]=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Si:19]([O:26][C:27]1[CH:32]=[C:31]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH:30]=[CH:29][C:28]=1[C@H:41]1[CH2:46][CH2:45][C@H:44]([OH:47])[CH2:43][CH2:42]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>ClCCl>[C:10]1([NH:16][C:17](=[O:18])[O:47][C@H:44]2[CH2:43][CH2:42][C@H:41]([C:28]3[CH:29]=[CH:30][C:31]([O:33][Si:34]([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:36])[CH3:35])=[CH:32][C:27]=3[O:26][Si:19]([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:21])[CH3:20])[CH2:46][CH2:45]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 178455059HCID 178455059, compound

Product 1

HCID 178455061HCID 178455061, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (100 μl) and phenylisocyanate (55 μl) were added to a stirred solution of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (50 mg) in anhydrous dichloromethane (2 ml). After 96 hr at 40° C., the reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous layer was extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with brine (50 ml); dried over magnesium sulfate and evaporated in vacuo. The residue was purified using flash column chromatography (SiO2, ethyl acetate/petrol, 1:2 v/v) to give the title compound (50 mg, 79%) as a pale yellow gum. δH(CDCl3) 0.00 (6H, s), 0.06 (6H, s), 0.80 (9H, s), 0.83 (9H, s), 1.30-1.40 (4H, m), 1.70-1.75 (2H, m), 2.00-2.05 (2H, m), 2.60-2.70 (1H, m), 4.55-4.65 (1H, m), 6.10 (1H, d), 6.23 (1H, dd), 6.40 (1H, s), 6.76-7.20 (5H, m).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate (50 ml) and water (50 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 ml)
  3. washThe combined organic extracts were washed with brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-5a01c76afe684f4a9227b4262aa20444
Source dataset
uspto-grants-2004_09
Patent number
US06797731B2

Reaction notes

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