Diisobutylaluminum hydride → [3-Chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazol-4-yl]methanol

HRID 2177405Notes

Reaction equation

HRID 2177405 reaction equation
[Cl:1][C:2]1[C:6]([C:7](OCC)=[O:8])=[C:5]([C:12]2[CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH:13]=2)[S:4][N:3]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:6]([CH2:7][OH:8])=[C:5]([C:12]2[CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH:13]=2)[S:4][N:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 118184949Ethyl 3-chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazole-4-carboxylate

Product 1

HCID 118184947[3-Chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazol-4-yl]methanolYield 35.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 3-chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazole-4-carboxylate (150 mg, 0.52 mmol, 1.00 equiv), toluene (3 mL). DIBAL-H (0.926 mL) was added dropwise at −78° C. with stirring. The resulting solution was allowed to warm to 20° C. and then stirred for 1 h. The reaction was then quenched by the addition of MeOH. The resulting mixture was concentrated under reduced pressure. The residue was applied to a silica gel column, eluting with ethyl acetate/petroleum ether (20:80), to afford 45 mg (35%) of [3-chloro-5-(4-methylcyclohex-1-en-1-yl)-1,2-thiazol-4-yl]methanol as colorless oil.

Workup

  1. customInto a 25-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringstirred for 1 h
  4. customThe reaction was then quenched by the addition of MeOH
  5. concentrationThe resulting mixture was concentrated under reduced pressure
  6. washeluting with ethyl acetate/petroleum ether (20:80)

Sources & evidence

ORD record
ord-dc01dccecd1b446f80b4c91b1b55acdb
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…