Water → Tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate

HRID 626837노트

반응식

HRID 626837 반응식
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([CH:21]=[CH2:22])[C:7]([C:23]#[N:24])=[C:6]([Cl:25])[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[Cl:25][C:6]1[CH:5]=[C:4]([CH:1]([OH:3])[CH3:2])[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[C:8]([CH:21]=[CH2:22])[C:7]=1[C:23]#[N:24]

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86697528Tert-butyl [2-(6-acetyl-4-chloro-3-cyano-2-vinylphenoxy)ethyl]carbamate

생성물 1

HCID 86697529Tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate수율 100%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Tert-butyl [2-(6-acetyl-4-chloro-3-cyano-2-vinylphenoxy)ethyl]carbamate (1.6 g, 4.4 mmol) was dissolved in methanol (40 mL) cooled in an ice bath and the sodium tetrahydroborate (0.16 g, 4.4 mmol) was added. The reaction was stirred for 1 h and water was added to quench residual hydride and the reaction was concentrated to remove the methanol. The aqueous was diluted with ethyl acetate washed with brine, dried over magnesium sulfate and concentrated to give tert-butyl {2-[4-chloro-3-cyano-6-(1-hydroxyethyl)-2-vinylphenoxy]ethyl}carbamate as a glass (1.6 g, 100%). LCMS calculated for C18H23ClN2O4Na (M+Na)+: m/z=389.1; found: 389.1.

후처리

  1. temperaturecooled in an ice bath
  2. customto quench residual hydride
  3. concentrationthe reaction was concentrated
  4. customto remove the methanol
  5. additionThe aqueous was diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-985d1c5a7ed945d7bca61e995a8354a8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309251B2

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