Methanol → 1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanol

HRID 404869Notes

Reaction equation

HRID 404869 reaction equation
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([C:20](=[O:22])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].CO.[BH4-].[Na+]>O1CCCC1>[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([OH:22])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 694364601-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanone

Product 1

HCID 694373051-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethanolYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 3A (320 mg, 0.89 mmol) in a mixture of 1:1 methanol:tetrahydrofuran (40 mL) was added sodium borohydride (67.5 mg, 1.78 mmol) and stirred at room temperature for 2.5 hours. The reaction mixture was quenched with acetone, the solvent removed in vacuum and the residue dissolved in dichloromethane. The organic phase was washed with water and brine, dried over magnesium sulfate filtered and evaporated, to produce the title compound (317 mg). 1H NMR (300 MHz, CDCl3) δ ppm 7.15-7.29 (m, 3H) 6.82-6.97 (m, 4H) 502-5.16 (m, 1H) 4.43-4.61 (heptet, J=6.25 Hz, 1H) 1.60 (d, J=6.62 Hz, 3H) 1.35 (d, J=6.25 Hz, 6H). MS (DCI): m/z 362 (M+H).

Workup

  1. customThe reaction mixture was quenched with acetone
  2. customthe solvent removed in vacuum
  3. dissolutionthe residue dissolved in dichloromethane
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-e1b134c4ec7948afa5c0028a2a40379c
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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