Methyl 4-oxobutyrate → Dimethyl 3-formyl-4-hydroxyheptanedioate

HRID 593415

反応式

HRID 593415 の反応式
[O:1]=[CH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]>CN(C=O)C>[CH:2]([CH:3]([CH:2]([OH:1])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:1]

参加物

3

反応物 1

HCID 83779Methyl 4-oxobutyrate

生成物 1

HCID 123250817Dimethyl 3-formyl-4-hydroxyheptanedioate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(S)-Proline (14.9 mg, 0.13 mmol) was added to a stirred solution of 16 (150 mg, 1.29 mmol) in THF (650 μl). The reaction mixture was stirred at r.t. for 14 h. The reaction mixture was purified directly by column chromatography, eluting with petrol/EtOAc (2:1), to give the aldehydes 17 and SI-3 (as a 3.6:1 mixture of anti:syn diastereoisomers, 91 mg, 61%) as a clear colourless oil. The reaction was also conducted on a 244 mg scale of aldehyde 16 in DMF which gave a 2:1 ratio of anti:syn diastereoisomers (100 mg, 41%).

後処理

  1. additionas a 3.6:1 mixture of anti
  2. customgave a 2:1 ratio of anti

出典と根拠

ORDレコード
ord-e39d86288885447bbe8053d407512a87
出典データセット
uspto-grants-2016_01
特許番号
US09242954B2

関連ノート

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