Aluminium lithium hydride → HCID 90418236, compound

HRID 2177184Notes

Reaction equation

HRID 2177184 reaction equation
[F:1][C:2]1([F:21])[CH2:6][CH2:5][CH:4]([C:7]2[C:11]([C:12](OCC)=[O:13])=[C:10]([C:17]([F:20])([F:19])[F:18])[S:9][N:8]=2)[CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[F:21][C:2]1([F:1])[CH2:6][CH2:5][CH:4]([C:7]2[C:11]([CH2:12][OH:13])=[C:10]([C:17]([F:19])([F:20])[F:18])[S:9][N:8]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90418402HCID 90418402, compound

Product 1

HCID 90418236HCID 90418236, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Into a 100-mL round-bottom flask, was placed ethyl 3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate (200 mg, 0.61 mmol, 1.00 equiv), ether (5 mL), LAH (46 mg, 1.21 mmol, 2.00 equiv). The resulting solution was stirred for 1 h at 0° C. The reaction was then quenched by the addition of 10 ml of EA. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/30-1/10). This resulted in 100 mg (crude) of [3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 10 ml of EA
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 100 mg (crude) of [3-(3,3-difluorocyclopentyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as yellow oil

Sources & evidence

ORD record
ord-61bc7f1b9e834975b76e44eddc2fa33d
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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