1-Ethoxy-2,2-difluoroethanol → HCID 178445928, compound

HRID 2223519Notes

Reaction equation

HRID 2223519 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH2:15])[CH2:11][CH:12]([CH3:14])[CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O[CH:19](O)[CH:20]([F:22])[F:21])C>C1C=CC=CC=1>[Si:1]([O:8][CH2:9][C@@H:10](/[N:15]=[CH:19]/[CH:20]([F:22])[F:21])[CH2:11][CH:12]([CH3:13])[CH3:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27582461-Ethoxy-2,2-difluoroethanolHCID 11345273{[(2S)-2-amino-4-methylpentyl]oxy}(tert-butyl)dimethylsilane

Product 1

HCID 178445928HCID 178445928, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (2S)-1-{[tert-butyl(dimethyl)silyl]oxy}-4-methylpentan-2-amine (8.5 g, 36.8 mmol) and difluoroacetaldehyde ethyl hemiacetal (5.0 g, 39.7 mmol) in benzene was refluxed with a Dean-stark trap overnight. Solvent was removed in vacuo. The residue was passed through a short silica column and eluted with hexanes:EtOAc (10:1) to give the title compound as a pale yellow oil.

Workup

  1. temperaturewas refluxed with a Dean-stark trap overnight
  2. customSolvent was removed in vacuo
  3. washeluted with hexanes:EtOAc (10:1)

Sources & evidence

ORD record
ord-a9780a30645a494da23a6784487e54f0
Source dataset
uspto-grants-2008_05
Patent number
US07375134B2

Reaction notes

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