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

HRID 1719629Notes

Reaction equation

HRID 1719629 reaction equation
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]C)[CH2:15][C@H:14]([O:20]CC3C=CC=CC=3)[CH2:13]2)(=O)=O)C=CC=CC=1.P(O)([O-])([O-])=O.[Na+].[Na+].O>CO.[Na].[Hg]>[Cl:35][C:29]1[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:28]=1[CH2:10][CH2:11][C@@H:12]1[O:17][C:16](=[O:18])[CH2:15][C@H:14]([OH:20])[CH2:13]1

Participants

6

Reactant 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

Product 1

HCID 13186032(4R,6S) 6-[2-(2,4-dichlorophenyl)ethyl]-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-onYield 125.8%

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalyst2×HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-993701b409a842018010fc2d9c36be7f
Source dataset
uspto-grants-1985_09
Patent number
US04540796

Reaction notes

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