HCID 90418268, compound → HCID 90418044, compound

HRID 2177296Notes

Reaction equation

HRID 2177296 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][N:12]=[C:11]([CH3:14])[C:10]=1[C:15](O)=[O:16]>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][N:12]=[C:11]([CH3:14])[C:10]=1[CH2:15][OH:16]

Participants

3

Reactant 1

HCID 90418268HCID 90418268, compound

Product 1

HCID 90418044HCID 90418044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 25-mL round-bottom flask, was placed 5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazole-4-carboxylic acid (180 mg, 0.72 mmol, 1.00 equiv), tetrahydrofuran (10 mL). This was followed by the addition of BH3 (2.1 mL) at 0-5° C. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:3). This resulted in 100 mg (59%) of [5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazol-4-yl]methanol as a white solid.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. additionThis was followed by the addition of BH3 (2.1 mL) at 0-5° C
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 100 mg (59%) of [5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazol-4-yl]methanol as a white solid

Sources & evidence

ORD record
ord-de192c5f5fd84548a95723437b782a9c
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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