Triethylamine → (S)-4-O-Benzyl-1-O-[(p-methoxyphenyl)diphenylmethyl]-1,2,4-butanetriol

HRID 1939706Notes

Reaction equation

HRID 1939706 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([OH:14])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:20][CH3:21])CC)C.C([C:31](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)C1C=CC(OC)=CC=1.[C:45](=[O:48])(O)[O-].[Na+]>C(Cl)Cl.CN(C1C=CC=CN=1)C>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([OH:14])[CH2:12][O:13][C:31]([C:21]1[CH:20]=[CH:4][C:3]([O:48][CH3:45])=[CH:2][CH:1]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9794180(S)-4-Benzyloxy-1,2-butanediolHCID 14836583p-Anisyldiphenylmethyl chloride

Product 1

HCID 14632462(S)-4-O-Benzyl-1-O-[(p-methoxyphenyl)diphenylmethyl]-1,2,4-butanetriolYield 95%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-4-O-Benzyl-1,2,4-butanetriol (68.3 g, 348 mmol) was mixed with triethylamine (70.4 g, 696 mmol) and dimethylaminopyridine (3.42 g, 28 mmol) were mixed in methylene chloride (300 mL) under nitrogen atmosphere. To the solution p-anisylchlorodiphenylmethane (129.1 g, 418 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 5 hours. Saturated sodium bicarbonate was added to the mixture and the resulting mixture was stirred at room temperature for 1 hour. The aqueous layer was extracted with methylene chloride (150 mL×2). The combined methylene chloride extracts were dried over mganesium sulfate. The solvent was evaporated, and the residue was purified by flash chromatography on silica gel (ethyl acetate:hexane=1:5 to 1:1) to give 155.5 g (95% yield) of the title compound as a thick oil.

Workup

  1. waitat room temperature for 5 hours
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. extractionThe aqueous layer was extracted with methylene chloride (150 mL×2)
  4. dry with materialThe combined methylene chloride extracts were dried over mganesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by flash chromatography on silica gel (ethyl acetate:hexane=1:5 to 1:1)

Sources & evidence

ORD record
ord-2287e7b6818e4e659bb1199ff9412195
Source dataset
uspto-grants-1997_12
Patent number
US05696263

Reaction notes

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