Boron trifluoride etherate → HCID 86032840, compound

HRID 1454096Notes

Reaction equation

HRID 1454096 reaction equation
B(F)(F)F.CCOCC.[CH2:10]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1)[CH2:11][CH:12]([CH3:14])[CH3:13].[C:26](OC(=N)C(Cl)(Cl)Cl)([CH3:29])([CH3:28])[CH3:27]>C1COCC1>[CH2:10]([O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:20][CH:21]=1)[CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8216954-(3-Methylbutoxy)benzeneacetic acid2×HCID 2734700Tert-butyl 2,2,2-trichloroethanimidate

Product 1

HCID 86032840HCID 86032840, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boron trifluoride etherate (0.65 mL) was added in one portion to a stirred solution of [4-(isopentyloxy)phenyl]acetic acid (crude from preparation of intermediate 11; 7.31 g, 32.9 mmol) and t-butyltrichloroacetimidate (14.4 g, 11.8 mL, 65.8 mmol) in THF (70 mL) at room temperature under nitrogen. The resulting solution was stirred for 16 h then quenched with saturated aqueous sodium hydrogen carbonate solution (50 mL). The resulting suspension was extracted with ethyl acetate (3×50 mL) then the organic_extracts combined, dried_(magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (5-10% diethyl ether: cyclohexane) to give the title compound as a colourless oil (3.82 g, 42% over 2 steps). LC/MS: 3.94 min; z/e 296, calcd (M+18) 296. 1H NMR (400 MHz: CDCl3): 7.25 (2H), 6.90 (2H), 4.05 (2H), 3.55 (2H), 1.90 (1H), 1.75 (2H), 1.50 (9H), 1.05 (6H).

Workup

  1. customthen quenched with saturated aqueous sodium hydrogen carbonate solution (50 mL)
  2. extractionThe resulting suspension was extracted with ethyl acetate (3×50 mL)
  3. customdried_(magnesium sulfate) and evaporated to dryness
  4. customThe residue was chromatographed on silica gel (5-10% diethyl ether: cyclohexane)

Sources & evidence

ORD record
ord-3f297daee54e4df7bf8848d2a139588c
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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