Acetyl chloride → HCID 21202087, compound

HRID 1978903Notes

Reaction equation

HRID 1978903 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:16])([C:12]([F:15])([F:14])[F:13])[O:7][CH2:6][CH2:5]2.C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25]>C1COCC1>[C:24]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:16])([C:12]([F:15])([F:13])[F:14])[O:7][CH2:6][CH2:5]2)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21202093HCID 21202093, compound

Product 1

HCID 21202087HCID 21202087, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-hydroxy-1-methyl-1-trifluoromethylisochroman (79 g, 0.34 mol) and triethylamine (120 mL, 0.88 mol) in THF (680 mL) was added acetyl chloride (31 mL, 0.44 mol) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction was quenched by adding aqueous 1 N-HCl (400 mL), and extracted with ethyl acetate (500 mL). The extracts were washed with aqueous saturated NaHCO3 (100 mL) and brine (100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography (Silica-gel, 15×20 cm, 6% ethyl acetate/hexane) to afford 6-acetoxy-1-methyl-1-trifluoromethylisochroman (83 g, 89%) as a colorless oil. 1H-NMR(CDCl3): 7.36 (d, J=7.2 Hz, 1H), 6.98 (dd, J=7.2, 2.5 Hz, 1H), 6.91 (d, J=2.5 Hz, 1H), 4.18-4.08 (m, 1H), 3.92 (dt, J=11, 5.4 Hz, 1H), 2.86 (t, J=5.4 Hz, 2H), 2.30 (s, 1H), 1.66 (s, 3H).

Workup

  1. customThe reaction was quenched
  2. additionby adding aqueous 1 N-HCl (400 mL)
  3. extractionextracted with ethyl acetate (500 mL)
  4. washThe extracts were washed with aqueous saturated NaHCO3 (100 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (Silica-gel, 15×20 cm, 6% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-10471732ec5e41d9a035fa1a31fc28af
Source dataset
uspto-grants-2001_05
Patent number
US06239147B1

Reaction notes

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