Hydrochloric Acid → HCID 15136264, compound

HRID 981271Notes

Reaction equation

HRID 981271 reaction equation
[C:1]([CH:4]1[CH2:6][CH:5]1[C:7]1[C:17]([F:18])=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([F:19])[C:8]=1[F:20])(O)=[O:2].B.C(OCC)(=O)C.Cl>O1CCCC1.O>[OH:2][CH2:1][CH:4]1[CH2:6][CH:5]1[C:7]1[C:17]([F:18])=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([F:19])[C:8]=1[F:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 8857Ethyl AcetateHCID 15136262Ethyl 4-(2-carboxycyclopropyl)-2,3,5-trifluorobenzoate

Product 1

HCID 15136264HCID 15136264, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In 60 ml of anhydrous tetrahydrofuran was dissolved 6.00 g of ethyl 4-(2-carboxycyclopropyl)-2,3,5-trifluorobenzoate. To the resulting solution was added 42 ml of a 1M solution of borane in tetrahydrofuran with ice-cooling. The resulting mixture was stirred for 1.5 hours at room temperature. The reaction mixture was added to a mixture of 100 ml of ethyl acetate and 100 ml of water. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene/ethyl acetate=4/1) to obtain 4.40 g (yield: 77.1%) of ethyl 4-(2-hydroxymethylcyclopropyl)-2,3,5-trifluorobenzoate.

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue obtained
  7. customwas purified by a column chromatography (eluant: toluene/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-8c06ac7f829a46d1ba2058676628b65c
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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