Ethyl Acetate → [2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]methanol

HRID 1498914Notes

Reaction equation

HRID 1498914 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]([C:20](O)=[O:21])=[C:17]([CH3:19])[N:18]=2)=[C:10]([O:23][CH3:24])[CH:9]=1.C(OCC)(=O)C>O1CCCC1.C(=O)(O)[O-].[Na+]>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]([CH2:20][OH:21])=[C:17]([CH3:19])[N:18]=2)=[C:10]([O:23][CH3:24])[CH:9]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 686420482-(4-Chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 68641830[2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]methanolYield 43%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalyst2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (380 mg, 10.0 mmol) was suspended in tetrahydrofuran (10 ml), and a suspension (10 ml) of 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid (1.42 g, 5.00 mmol) prepared in Example 7-1 in tetrahydrofuran was added thereto at a room temperature. The mixture was stirred for 3 hours at a room temperature. Under an ice cooling, 5 drops of a saturated sodium bicarbonate solution were slowly added to the mixture. Ethyl acetate was added to the mixture, and another 5 drops of a saturated sodium bicarbonate solution were added thereto. The precipitate was removed by filtration, and the removed solid was washed with chloroform. The washings and the filtrate were concentrated together. The concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1) to give the title compound (580 mg, 43%) as a light-brown powder.

Workup

  1. customat a room temperature
  2. customThe precipitate was removed by filtration
  3. washthe removed solid was washed with chloroform
  4. concentrationThe washings and the filtrate were concentrated together
  5. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-51a779d5609a46cd9dc52d2306de1c7e
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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