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

HRID 1939706
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HRID 1939706 반응식
[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
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 21885
2-Dimethylaminopyridine
촉매
HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2287e7b6818e4e659bb1199ff9412195
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05696263

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