3-Chloro-5-(2-methylphenyl)-1,2-thiazole-4-carboxylic acid → [3-Chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol

HRID 2177275Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 100-mL round-bottom flask, was placed 3-chloro-5-(2-methylphenyl)-1,2-thiazole-4-carboxylic acid (3 g, 11.82 mmol, 1.00 equiv), tetrahydrofuran (30 mL). This was followed by the addition of BH3(1M) (30 mL) dropwise with stirring at 0° C. The resulting solution was stirred overnight at 30° C. The reaction was then quenched by the addition of 30 mL of methanol. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (26/84). The collected fractions were combined and concentrated under vacuum. This resulted in 260 mg (9%) of [3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol as yellow oil.

Workup

customInto a 100-mL round-bottom flask, was placed
additionThis was followed by the addition of BH3(1M) (30 mL) dropwise
stirringThe resulting solution was stirred overnight at 30° C
customThe reaction was then quenched by the addition of 30 mL of methanol
concentrationThe resulting mixture was concentrated under vacuum
concentrationconcentrated under vacuum
customThis resulted in 260 mg (9%) of [3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol as yellow oil

Sources & evidence

ORD record: ord-f383fa4bdb99477fb3f5cf11eb08a899
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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