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

HRID 325542

반응식

HRID 325542 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9837419Sodium amalgam촉매2회HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1907b127c72c41479c8544c82f587d97
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04440927

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