Boron trifluoride etherate → HCID 69561770, compound

HRID 1633867Notes

Reaction equation

HRID 1633867 reaction equation
O[CH2:2][CH2:3][CH:4]([C:7]1[CH:8]=[C:9]([CH:19]=[CH:20][C:21]2[CH:30]=[C:29]3[C:24]([CH2:25][CH2:26][N:27]=[C:28]3[CH:31]([CH3:33])[CH3:32])=[CH:23][CH:22]=2)[CH:10]=[C:11]2[C:16]=1[CH:15]=[C:14]([C:17]#[N:18])[CH:13]=[CH:12]2)[CH2:5][OH:6].C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[CH:31]([C:28]1[C:29]2[C:24](=[CH:23][CH:22]=[C:21]([CH:20]=[CH:19][C:9]3[CH:10]=[C:11]4[C:16](=[C:7]([CH:4]5[CH2:3][CH2:2][O:6][CH2:5]5)[CH:8]=3)[CH:15]=[C:14]([C:17]#[N:18])[CH:13]=[CH:12]4)[CH:30]=2)[CH2:25][CH2:26][N:27]=1)([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 69561943HCID 69561943, compound

Product 1

HCID 69561770HCID 69561770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 7A (140 mg, 0.52 mmol) in dichloromethane (3 mL) at 0° C. was treated with triethylsilane (0.166 mL, 1.04 mmol) and BF3.OEt2 (0.096 mL, 0.78 mmol), warmed to room temperature, stirred for 4 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-974c6f8d59a84075945cf15a29e3f5e8
Source dataset
uspto-grants-2003_01
Patent number
US06504031B1

Reaction notes

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