Methanol → HCID 53948356, compound

HRID 1420851Notes

Reaction equation

HRID 1420851 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.C(Cl)(Cl)(Cl)[Cl:43]>>[CH2:1]([O:8][CH2:9][C@@H:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:11][Cl:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 56987842HCID 56987842, compound

Product 1

HCID 53948356HCID 53948356, compound

Procedure

A solution of (2S)-3-benzyloxy-2-(2-methoxyphenyl)propan-1-ol (Description 98, 2 g, 7.4 mmol) and triphenylphosphine (2.12 g, 8.1 mmol) in carbon tetrachloride (10 mL) was heated in an oil bath at 100° C. for 5 h. Methanol (1 mL) was cautiously added and the mixture was cooled to room temperature and stirred for 16 h. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel, eluting with hexane/EtOAc (100:0 increasing to 95:5) to give the title compound (1.5 g). 1H NMR (250 MHz, CDCl3) δ7.37-7.2 (7 H, m), 6.96-6.86 (2 H, m), 4.54 (2 H, s), 3.92 (2 H, m), and 3.81-3.73 (7 H, m).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel
  3. washeluting with hexane/EtOAc (100:0 increasing to 95:5)

Sources & evidence

ORD record
ord-d3bd4c519191431b96184ef1c5116ee4
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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