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

HRID 1939706
ノート
印刷プレビュー

反応式

HRID 1939706 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 21885
2-Dimethylaminopyridine
触媒
HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-2287e7b6818e4e659bb1199ff9412195
出典データセット
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05696263

反応ノート

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