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

HRID 593415

반응식

HRID 593415 반응식
[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]

참가 물질

3

반응물 1

HCID 83779Methyl 4-oxobutyrate

생성물 1

HCID 123250817Dimethyl 3-formyl-4-hydroxyheptanedioate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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%).

후처리

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

출처 및 근거

ORD 기록
ord-e39d86288885447bbe8053d407512a87
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242954B2

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