Cyclohexyl isocyanate → HCID 178455062, compound

HRID 585679Notes

Reaction equation

HRID 585679 reaction equation
[CH:1]1([N:7]=[C:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Si:10]([O:17][C:18]1[CH:23]=[C:22]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH:21]=[CH:20][C:19]=1[CH:32]1[CH2:37][CH2:36][CH:35]([OH:38])[CH2:34][CH2:33]1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>ClC(Cl)C>[CH:1]1([NH:7][C:8](=[O:9])[O:38][C@H:35]2[CH2:34][CH2:33][C@H:32]([C:19]3[CH:20]=[CH:21][C:22]([O:24][Si:25]([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:27])[CH3:26])=[CH:23][C:18]=3[O:17][Si:10]([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:12])[CH3:11])[CH2:37][CH2:36]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 22337761HCID 22337761, compound

Product 1

HCID 178455062HCID 178455062, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

N,N-Diisopropylethylamine(199 μl) and cyclohexyl isocyanate (128 μl) were added to a stirred solution of 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (50 mg) in dry dichloroethane (1 ml) at room temperature under argon. The reaction mixture was heated to 40° C. for 120 h, and was partitioned between water (50 ml) and ethyl acetate (50 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 ml). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:2 v/v) to give the title compound as a pale yellow solid (30 mg, 47%); δH (CDCl3) 0.12 (6H, s), 0.18 (6H, s), 0.90 (9H, s), 0.95 (9H, s). 1.00-2.10 (18H, m), 2.70-2.80 (1H, m), 3.36-3.50 (1H, m), 4.40-4.48 (1H, m), 4.50-4.62 (1H, m), 6.20 (1H, d), 6.32 (1H, dd), 6.86 (1H, d).

Workup

  1. customwas partitioned between water (50 ml) and ethyl acetate (50 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×50 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:2 v/v)

Sources & evidence

ORD record
ord-7d7613b31c3344d6ab24f8088b2bd06a
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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