Diethyl Ether → HCID 57137252, compound

HRID 982188Notes

Reaction equation

HRID 982188 reaction equation
[C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])(=[O:3])[CH3:2].[C:9]([O:13][CH2:14][C@@H:15]([OH:21])[CH2:16][C:17](OC)=[O:18])([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+].C(OCC)C>C(=O)=O.CC(C)=O.O1CCCC1>[C:9]([O:13][CH2:14][C@@H:15]([OH:21])[CH2:16][C:17](=[O:18])[CH2:2][C:1]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3])([CH3:12])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10908tert-Butyl acetateHCID 25517Ammonium ChlorideHCID 57042781HCID 57042781, compound

Product 1

HCID 57137252HCID 57137252, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 18522661Acetone cardiceSolvent

Procedure

After completion of the dropwise addition, the mixture was stirred for 15 minutes to synthesize a lithium enolate of t-butyl acetate. The reaction mixture was cooled to -50° C. in dry ice-acetone, and a solution of 3.3 g (16.5 mmole) of methyl (3S)-4-t-butoxy-3-hydroxybutanoate as prepared in Example 1 in 15 ml of tetrahydrofuran was added to the mixture through the dropping funnel over 20 minutes, followed by stirred for an additional 1.5 hours. After confirming the completion of the reaction by gas chromatography, 30 ml of a saturated aqueous solution of ammonium chloride and 100 ml of diethyl ether were added to the reaction mixture to conduct extraction. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (diethyl ether/hexane: 1/1 by volume) to obtain 2.3 g (yield: 46%) of t-butyl (5S)-6-t-butoxy-5-hydroxy-3-oxohexanoate.

Workup

  1. additionAfter completion of the dropwise addition
  2. additionwas added to the mixture through the dropping funnel over 20 minutes
  3. stirringby stirred for an additional 1.5 hours
  4. additionwere added to the reaction mixture
  5. extractionextraction
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation
  8. customThe residue was purified by silica gel column chromatography (diethyl ether/hexane: 1/1 by volume)

Sources & evidence

ORD record
ord-c5147585c39d465fa09612ac761f95c2
Source dataset
uspto-grants-1991_02
Patent number
US04994602

Reaction notes

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