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Sulfuric Acid → 2(R)-(p-tert-butyl-benzyl)-3-methyl-butanol

HRID 725585
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HRID 725585 반응식
[CH:1]([C@@H:4]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)[C:5](N1[C@H](CC2C=CC=CC=2)COC1=O)=[O:6])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.S(=O)(=O)(O)O>O1CCCC1.O1CCCC1.O>[CH:1]([C@@H:4]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([CH3:29])([CH3:28])[CH3:30])=[CH:25][CH:26]=1)[CH2:5][OH:6])([CH3:3])[CH3:2]
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참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 228657663-[2(R)-isopropyl-3(p-tert-butyl-phenyl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

생성물 1

HCID 228657362(R)-(p-tert-butyl-benzyl)-3-methyl-butanol

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
2회
HCID 21881883Oxolane--water (1/1)용매

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온도
0 °C

실험 절차

With stirring at 0° C., a solution of 8.63 g of 3-[2(R)-isopropyl-3-(p-tert-butyl-phenyl)propanoyl]-4(R)-benzyl-oxazolidin-2-one in 40 ml of tetrahydrofuran is added dropwise to a suspension of 2.41 g of LiAlH4 in 160 ml of tetrahydrofuran. The reaction mixture is stirred for a further 4 hours at 0° C. and then, at 0° C., 5 ml of ethyl acetate, 30 ml of a mixture of tetrahydrofuran/water=1:1 and then 80 ml of 2N sulfuric acid are added in succession thereto. The suspension is extracted with ethyl acetate and the extracts are concentrated by evaporation and purified by FC (700 g of silica gel, eluant: dichloromethane). The title compound is obtained: Rf (dichloromethane)=0.34; m.p.=49°-51° C.

후처리

  1. stirringThe reaction mixture is stirred for a further 4 hours at 0° C.
  2. extractionThe suspension is extracted with ethyl acetate
  3. concentrationthe extracts are concentrated by evaporation
  4. custompurified by FC (700 g of silica gel, eluant: dichloromethane)

출처 및 근거

ORD 기록
ord-87badfc5a6cb4f8eb623a15a8fdb679c
출처 데이터셋
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05705658

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