Allyltrimethylsilane → HCID 22884183, compound

HRID 1597832Notes

Reaction equation

HRID 1597832 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]([O:8][CH2:9][C@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12](S(C2C=CC=CC=2)(=O)=O)[O:11]1)(=[O:7])[CH3:6].[CH2:25]([Si](C)(C)C)[CH:26]=[CH2:27]>ClCCl>[C:5]([O:8][CH2:9][C@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([CH2:27][CH:26]=[CH2:25])[O:11]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 69808AllyltrimethylsilaneHCID 6451240Aluminum(III) ChlorideHCID 54210485HCID 54210485, compound

Product 1

HCID 22884183HCID 22884183, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Aluminium trichloride (1 g) was cooled to -78° C. under a nitrogen atmosphere and dichloromethane (15 ml) was added. A solution of trans-6-(benzenesulfonyl)tetrahydro-2H-pyran-2-methanol acetate (S. V. Ley et al., Tetrahedron (1989), 45 (13), 4293) (1 g) and allyl trimethylsilane (835 mg) in dichloromethane (10 ml) was then added dropwise. The reaction was stirred at -78° C. for 2 h, then -35° C. for 1 h. After quenching with 1N HCl and extracting with dichloromethane the crude product was purified by flash chromatography (40% EtOAc/hexane) to give the title compound of (414 mg).

Workup

  1. wait-35° C. for 1 h
  2. customAfter quenching with 1N HCl
  3. extractionextracting with dichloromethane the crude product
  4. customwas purified by flash chromatography (40% EtOAc/hexane)

Sources & evidence

ORD record
ord-8a1f1415f1404fb1ae97e109c6d5f378
Source dataset
uspto-grants-1998_04
Patent number
US05736549

Reaction notes

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