Ethyl isocyanate → HCID 178465492, compound

HRID 2307140Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

N,N-Diisopropylethylamine (199 μl) and ethyl isocyanate (90 μl) were added to a stirred solution of trans-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 solid (55 mg, 95%); Rf (ethyl acetate/petrol, 1:2 v/v) 0.65.

Workup

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

Sources & evidence

ORD record: ord-baebf0aa69434e5badf8da6a930dcec4
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828460B2

Reaction notes

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