Ethyl Acetate → 2(R)-(p-tert-butyl-benzyl)-3-methyl-butanol

HRID 2258293Notes

Reaction equation

HRID 2258293 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:30])[C@H:15]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[CH:16]([CH3:18])[CH3:17])C1C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O1CCCC1.O>O1CCCC1>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@H:15]([CH:16]([CH3:17])[CH3:18])[CH2:14][OH:30])=[CH:25][CH:24]=1)([CH3:28])([CH3:27])[CH3:29]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 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 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4(R)-benzyl-3-[2(R)-(p-tert-butyl-benzyl)-3-methyl-butyryl]-oxazolidin-2-one (8.63 g) in tetrahydrofuran (40 ml) is added dropwise at 0° C., with stirring, to a suspension of lithium aluminium hydride (2.41 g) in tetrahydrofuran (160 ml). The reaction mixture is stirred for 4 hours at 0° C. and then, at 0° C., ethyl acetate (5 ml), 30 ml of a (1:1) mixture of tetrahydrofuran/water and 2N sulfudc acid (80 ml) are added in succession thereto. The supension is extracted with ethyl acetate and the crude product is 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. additionare added in succession
  2. extractionThe supension is extracted with ethyl acetate
  3. customthe crude product is purified by FC (700 g of silica gel, eluant dichloromethane)

Sources & evidence

ORD record
ord-c0c62f6152cf4fad8d0631ec4d9d2fd7
Source dataset
uspto-grants-1997_08
Patent number
US05659065

Reaction notes

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