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

HRID 626837ノート

反応式

HRID 626837 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-985d1c5a7ed945d7bca61e995a8354a8
出典データセット
uspto-grants-2016_04
特許番号
US09309251B2

反応ノート

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