Boron trifluoride etherate → HCID 12134925, compound

HRID 1893171Notes

Reaction equation

HRID 1893171 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:22])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)O)[CH3:2].B(F)(F)F.CCOCC.C([SiH](CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:30])[C:5]([O:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([CH3:22])[CH2:6][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 12134921HCID 12134921, compound

Product 1

HCID 12134925HCID 12134925, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenoxy-3-(4-benzyloxyphenyl)-3-hydroxy-2-methyl-propionic acid ethyl ester (20.4 g, 50 mmol) in anhydrous CH2Cl2 (200 mL) was cooled to 0° C. and treated with BF3-Et2O (6.12 mL, 50 mmol) and triethylsilane (8.16 mL, 9.5 mmol). The mixture was stirred over night. Saturated aqueous Na2CO3 (75 mL) was added and the mixture was stirred vigorously. The solution was partitioned and the organic layer was washed twice with water and brine, dried over MgSO4 and concentrated in vacuo, then purified in silica to provide a colorless oil (9.9 g, 51%)

Workup

  1. stirringthe mixture was stirred vigorously
  2. customThe solution was partitioned
  3. washthe organic layer was washed twice with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified in silica

Sources & evidence

ORD record
ord-bed9dd997415490fa7cf1197e8a85a1a
Source dataset
uspto-grants-2013_08
Patent number
US08513233B2

Reaction notes

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