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

HRID 744776
Notes
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Reaction equation

HRID 744776 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8ace3a35be6642b7aeaf84092c962322
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05559111

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes