Boron trifluoride etherate → HCID 76603827, compound

HRID 1182456Notes

Reaction equation

HRID 1182456 reaction equation
[CH3:1][C:2](=[CH:10][CH:11]([CH3:24])[CH:12](OC)[C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1)[CH:3]=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:1][C:2](=[CH:10][CH:11]([CH3:24])[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]([CH3:20])[CH3:21])=[CH:17][CH:18]=1)[CH:3]=[CH:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 72480332HCID 72480332, compound

Product 1

HCID 76603827HCID 76603827, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ester compound 31 (99 mg, 0.299 mmol) in CH2Cl2 (3 mL) at 0° C. was added triethylsilane (41.9 mg, 0.36 mmol) followed by BF3.Et2O (51 mg, 0.36 mmol) dropwise via microsyringe, and the mixture was stirred at 0° C. for 30 min. The reaction was quenched with saturated NaHCO3 solution (3 mL), diluted with CH2Cl2 (20 mL), and washed with water, and the organic phase was dried and concentrated. Purification by flash silica gel chromatography (10% ethyl acetate in hexane) afforded the title compound 36 (87 mg, 97% yield) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.29 (dd, J=15.6, 0.6 Hz, 1H), 6.98 (d, J=8.7 Hz, 2H), 6.64 (d, J=8.7 Hz, 2H), 5.74 (d, J=15.6 Hz, 1H), 5.73 (br d, J=10.2 Hz, 1H), 4.20 (q, J=6.9 Hz, 2H), 2.90 (s, 6H), 2.73 (m, 1H), 2.53 (d, J=7.2 Hz, 2H), 1.61 (d, J=0.6 Hz, 3H), 1.29 (t, J=6.9 Hz, 3H), 1.00 (d, J=6.6 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 12.1, 14.3, 20.0, 35.5, 40.8, 42.2, 60.1, 112.7, 115.5, 128.1, 129.7, 131.6, 147.5, 149.0, 149.8, 167.5.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution (3 mL)
  2. additiondiluted with CH2Cl2 (20 mL)
  3. washwashed with water
  4. customthe organic phase was dried
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2ce8fb08091443e8af231ad1a3793f36
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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