(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 2226985ノート

反応式

HRID 2226985 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-66974f4d285c4dc88cfc292f7f171e54
出典データセット
uspto-grants-1994_09
特許番号
US05350760

反応ノート

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