Benzyl acetate → HCID 58059648, compound

HRID 1842568Notes

Reaction equation

HRID 1842568 reaction equation
[Si:1]([O:8][CH:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:28]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:30])[CH3:29].[Li+].CC([N-]C(C)C)C>C1COCC1>[Si:1]([O:8][CH:9]([CH:13]([CH3:15])[CH3:14])[C:10](=[O:12])[CH2:29][C:28]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8785Benzyl acetateHCID 682631,1'-CarbonyldiimidazoleHCID 2724682Lithium diisopropylamideHCID 14358765HCID 14358765, compound

Product 1

HCID 58059648HCID 58059648, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-{[tert-butyl(dimethyl)silyl]oxy}-3-methylbutanoic acid (1.0 g, 4.3 mmol) in THF (14.3 mL) at 0° C. were added carbonyldiimidazole (1.05 g, 6.45 mmol). After 15 min, the mixture was allowed to warm to ambient temperature and stirred for 48 h. This solution was cooled to −78° C. and added to a solution of preformed enolate by mixing benzyl acetate (2.18 mL, 15.1 mmol) and LDA (2.0 M in THF; 7.53 mL, 15.1 mmol) in THF (15 mL) at −78° C. The mixture was stirred at −78° C. for 1 h then warmed to −10° C. for 30 min. The mixture was cooled back to −78° C. and quenched with sat. NH4Cl. The mixture was extracted with dichloromehtane (3×). The combined organic extracts was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate) gave the title compound (0.43 g).

Workup

  1. temperatureThis solution was cooled to −78° C.
  2. stirringThe mixture was stirred at −78° C. for 1 h
  3. temperaturethen warmed to −10° C. for 30 min
  4. temperatureThe mixture was cooled back to −78° C.
  5. customquenched with sat. NH4Cl
  6. extractionThe mixture was extracted with dichloromehtane (3×)
  7. dry with materialThe combined organic extracts was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel chromatography (100% hexanes→75% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-b70ce3f17e004211a5796266f1bc83b5
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

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