(R)Methyl 1-(((1-(3-(hydroxymethyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)methyl)cyclopropaneacetate → Methyl 1-(((1 (R)-(3-formylphenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetate

HRID 2226985노트

반응식

HRID 2226985 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C@H:9]([S:22][CH2:23][C:24]2([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:26][CH2:25]2)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([OH:21])([CH3:20])[CH3:19])[CH:6]=[CH:7][CH:8]=1>CCOC(C)=O.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[C:5]([C@H:9]([S:22][CH2:23][C:24]2([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:25][CH2:26]2)[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([OH:21])([CH3:20])[CH3:19])[CH:6]=[CH:7][CH:8]=1)=[O:1]

참가 물질

4

반응물 1

HCID 18655248(R)Methyl 1-(((1-(3-(hydroxymethyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)methyl)cyclopropaneacetate

생성물 1

HCID 22857739Methyl 1-(((1 (R)-(3-formylphenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetate

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매3회HCID 8857Ethyl Acetate용매

실험 절차

To the dihydroxy ester from Step 15 (6.8 g, 15.4 mmol) in EtOAc (150 mL) at 50° C. was added MnO2 (6.7 g, 76.8 mmol). After stirring for 30 minutes at 50° C. more MnO2 (6.7 g) was added, and 30 minutes later, a third portion of MnO2 (6.7 g) was added. An hour later, the warm reaction mixture was filtered through celite and the cake was washed with additional EtOAc. Evaporation of the solvents gave the title aidehyde 5.62 g (83%). 1H NMR (CD3COCD3): δ5 10.4 (1H, s), 7.9 (1H, br s), 7.8 (2H, m), 7.58 (1H, t), 7.38 (1H, br d), 7.1 (3H, m), 4.1 (1H, t), 3.54 (3H, s), 3.13 (1H, ddd), 2.85 (1H, ddd), 2.51 (2H, s), 2.49 (2H, d), 2.2 (2H, m), 1.51 (6H, s), 0.52-0.32 (4H, m).

후처리

  1. additionwas added
  2. customAn hour later, the warm reaction mixture
  3. filtrationwas filtered through celite
  4. washthe cake was washed with additional EtOAc
  5. customEvaporation of the solvents
  6. customgave the title aidehyde 5.62 g (83%)

출처 및 근거

ORD 기록
ord-66974f4d285c4dc88cfc292f7f171e54
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05350760

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