Acetone → HCID 131737112, compound

HRID 60766Notes

Reaction equation

HRID 60766 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C:23](=[O:25])[CH2:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:36][C:37]([CH3:39])=[O:38]>O1CCCC1>[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C:23](=[O:25])[C@H:22]([C:37]([OH:38])([CH3:39])[CH3:36])[CH2:21]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 2733832Lithium HexamethyldisilazideHCID 11002733(S)-5-(((tert-Butyldiphenylsilyl)oxy)methyl)dihydrofuran-2(3H)-one2×

Product 1

HCID 131737112HCID 131737112, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution of (5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2-one (compound 40d, 5.00 g, 14.0 mmol) in dry tetrahydrofuran (28 mL) was added a solution of lithium bis(trimethylsilyl)azanide (1.3 M in THF, 11.8 mL, 15.4 mmol) dropwise at −78° C. under argon. After addition, the mixture was stirred at −78° C. for 1 hour. Then distilled acetone (1.23 mL, 15.4 mmol) was added dropwise to the mixture and the resulting mixture was stirred at −78° C. for another 2 hours. The reaction was quenched by saturated NH4Cl solution and extracted with EtOAc (30 mL) three times. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0-30% EtOAc in petroleum ether) to afford 5.7 g of (3S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1-hydroxy-1-methyl-ethyl)tetrahydrofuran-2-one (compound 40e) as a light yellow oil. MS obsd. (ESI+) [(M+NH4)+]: 430. (For the synthesis, please refer to: Tetrahedron 1997, 53, 6281-6294).

Workup

  1. additionAfter addition
  2. stirringthe resulting mixture was stirred at −78° C. for another 2 hours
  3. customThe reaction was quenched by saturated NH4Cl solution
  4. extractionextracted with EtOAc (30 mL) three times
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (eluting with 0-30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-e3dae6d1cb4d478a9910657e6c8958fe
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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