Triethylsilane → HCID 71014402, compound

HRID 714559Notes

Reaction equation

HRID 714559 reaction equation
[CH2:1]([O:8][CH2:9][C@@:10]12[CH2:15][C@@H:14]1[CH2:13][O:12][C:11]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:8][CH2:9][C@@:10]12[CH2:15][C@@H:14]1[CH2:13][O:12][CH2:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 71040664HCID 71040664, compound

Product 1

HCID 71014402HCID 71014402, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

The conditions in Sakai, N., et al. Synthesis, 2008 3533-3536 was used for this step. To a stirred mixture of (1R,5S)-1-((benzyloxy)methyl)-3-oxa-bicyclo[3.1.0]hexan-2-one (3b, 50 mmol) and InBr3 (1.0 mmol) in chloroform (200 mL) was added triethylsilane (200 mmol). The mixture was then heated and stirred at 65° C. for 16 h, then cooled to room temperature. The reaction was concentrated. The residue was purified by column (0-10 ethyl acetate in hexane) to give a colorless liquid as pure (1S,5S)-1-((benzyloxy)methyl)-3-oxa-bicyclo[3.1.0]hexane (3c). MS (ESI) m/z=205 (M+1).

Workup

  1. custom, et al. Synthesis, 2008 3533-3536
  2. temperatureThe mixture was then heated
  3. temperaturecooled to room temperature
  4. concentrationThe reaction was concentrated
  5. customThe residue was purified by column (0-10 ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1d9265c8cbc449b48131791d59d2d979
Source dataset
uspto-grants-2015_11
Patent number
US09187459B2

Reaction notes

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