Tetrahydrofuran → tert-butyl 4-[(1S)-1-hydroxyethyl]benzoate

HRID 80571노트

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HRID 80571 반응식
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].O1CCCC1.B(Cl)([C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.N(CCO)CCO>CCCCCC>[OH:3][C@H:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])=[CH:6][CH:5]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8113DiethanolamineHCID 11131038Chlorobis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)boraneHCID 13844704tert-Butyl 4-acetylbenzoate

생성물 1

HCID 70815081tert-butyl 4-[(1S)-1-hydroxyethyl]benzoate수율 103.3%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

To tert-butyl 4-acetylbenzoate (3.33 g) in a tetrahydrofuran (23 ml) solution, (−)-B-chlorodiisopinocampheylborane in a 65% hexane solution (11.2 ml) was added dropwise under ice cooling, then the mixture was stirred at that temperature for 1.5 hours. The reaction solution was concentrated, and the residue was diluted by diethyl ether. To the thus solution obtained, diethanolamine (4.3 ml) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The precipitates were removed by filtration, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=9/1 to 4/1) to obtain the title compound (3.47 g).

후처리

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was diluted by diethyl ether
  3. customTo the thus solution obtained
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. customThe precipitates were removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=9/1 to 4/1)

출처 및 근거

ORD 기록
ord-1a363a750112412691c011c2365672b9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846660B2

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