Ethyl Acetoacetate → ethyl (3R)-3-hydroxybutanoate

HRID 530274ノート

反応式

HRID 530274 の反応式
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]>CO>[OH:4][C@H:3]([CH3:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

参加物

3

反応物 1

HCID 8868Ethyl Acetoacetate

生成物 1

HCID 440030ethyl (3R)-3-hydroxybutanoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

Ethyl acetoacetate (7.5 g) and dry methanol (25 mL) were mixed and deoxygenated with flowing nitrogen for five minutes. The catalyst [(R)—Ru(BINAP)Cl2]2NEt3 (0.1 mol %) was added along with 2N HCl (0.1 mol %). The mixture was transferred to a standard Parr reactor apparatus and flushed by evacuating and refilling with hydrogen several times. The apparatus was heated at 50° C. with stirring under 100 psi of hydrogen for 16 h. After completion of reaction (monitored by TLC) the reaction was cooled and concentrated under reduced pressure. The residue was subjected to column chromatographic purification with petroleum ether/ethyl acetate (9:1 v/v) to get pure (R)-alcohol 43 as a colorless liquid.

後処理

  1. customdeoxygenated with flowing nitrogen for five minutes
  2. additionThe catalyst [(R)—Ru(BINAP)Cl2]2NEt3 (0.1 mol %) was added along with 2N HCl (0.1 mol %)
  3. customflushed
  4. customby evacuating
  5. customAfter completion of reaction (monitored by TLC) the reaction
  6. temperaturewas cooled
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was subjected to column chromatographic purification with petroleum ether/ethyl acetate (9:1 v/v)

出典と根拠

ORDレコード
ord-d15ce573f601488c9b6b67f4a2a73d3e
出典データセット
uspto-grants-2016_05
特許番号
US09353077B2

反応ノート

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