Hydrochloric Acid → HCID 67218422, compound

HRID 1505277Notes

Reaction equation

HRID 1505277 reaction equation
[BH4-].[Li+].C([O:5][C:6]([C:8]1[CH2:12][C:11]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=2)([C:13](F)(F)F)[O:10][N:9]=1)=O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CO>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([CH3:13])[O:10][N:9]=[C:8]([CH2:6][OH:5])[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4148881Lithium borohydrideHCID 58497921HCID 58497921, compound

Product 1

HCID 67218422HCID 67218422, compoundYield 123.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Lithiumborohydride (0.86 g, 39.7 mmol) was added in portions at ambient temperature to a solution of 5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester (8.8 g, 24.8 mmol) in tetrahydrofuran (100 ml) and a small amount of methanol (1.5 ml). After stirring for 2 h at 40° C. the reaction mixture was cooled to 20° C., made acidic with 2N hydrochloric acid and stirred for 1 h. Solid potassium carbonate was added until the reaction mixture was slightly alkaline. After extraction with ethylacetate the organic phase was separated, dried over sodium sulfate and concentrated to give 7.98 g of a white material which was used in the next step without further purification 1H-NMR (CDCl3, 400 MHz): 7.38-7.48 (m, 3H), 4.47 (d, 2H), 3.82 (d, 1H), 3.43 (d, 1H), 1.93 (t, 1H).

Workup

  1. temperaturewas cooled to 20° C.
  2. stirringstirred for 1 h
  3. extractionAfter extraction with ethylacetate the organic phase
  4. customwas separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b488271f8b6648ad987fb1ba74540cf3
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

Loading…