Water → 4(R)-Benzyloxy-6(S)-[2-(2,4-dichlorophenyl)ethyl]-2(R)-methoxy-3,4,5,6-tetrahydro-2H-pyran

HRID 325542

反応式

HRID 325542 の反応式
C1(S([CH:10]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[CH2:11][C@H:12]2[O:17][C@@H:16]([O:18][CH3:19])[CH2:15][C@H:14]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:13]2)(=O)=O)C=CC=CC=1.P(O)([O-])([O-])=O.[Na+].[Na+].O>CO.[Na].[Hg]>[CH2:21]([O:20][C@@H:14]1[CH2:13][C@H:12]([CH2:11][CH2:10][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=2[Cl:35])[O:17][C@@H:16]([O:18][CH3:19])[CH2:15]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 3

HCID 962WaterHCID 24203Sodium Phosphate, DibasicHCID 228261981-(2,4-dichlorophenyl)-2-(4(R)-benzyloxy-2(R)-methoxy-3,4,5,6-tetrahydro-2H-pyran-6(S)-yl)ethyl phenyl sulfone

生成物 1

HCID 228261994(R)-Benzyloxy-6(S)-[2-(2,4-dichlorophenyl)ethyl]-2(R)-methoxy-3,4,5,6-tetrahydro-2H-pyran収率 92%

試薬・触媒・溶媒 2

HCID 9837419Sodium amalgam触媒2 回HCID 887Methanol溶媒

実験手順

To a mixture of 1-(2,4-dichlorophenyl)-2-(4(R)-benzyloxy-2(R)-methoxy-3,4,5,6-tetrahydro-2H-pyran-6(S)-yl)ethyl phenyl sulfone (0.06 g, 0.11 mmole) and anhydrous disodium phosphate (0.065 g, 0.45 mmoles) in dry methanol (5 ml) was added pulverized 5% sodium amalgam (0.2 g). The mixture was stirred at room temperature for twenty hours, during which time an additional 0.4 g of 5% sodium amalgam was added in three portions. The reaction mixture was poured into water and extracted with ether. The ether solution was dried (MgSO4), filtered, and the solvent evaporated in vacuo to give the title compound as a colorless viscous oil (0.04 g); 'H NMR (CDCl3) δ 1.53 (1H, ddd), 1.58-1.88 (4H, m), 2.06 (1H, m), 2.70 (1H, ddd), 2.95 (1H, ddd), 3.42 (3H, s), 3.76 (1H, p), 4.16 (1H, d), 4.52 (1H, d), 4.65 (1H, d), 4.78 (1H, dd), 7.13-7.40 (8H, m).

後処理

  1. additionwas added
  2. additionwas added in three portions
  3. extractionextracted with ether
  4. dry with materialThe ether solution was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

出典と根拠

ORDレコード
ord-1907b127c72c41479c8544c82f587d97
出典データセット
uspto-grants-1984_04
特許番号
US04440927

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