Cerium(III) chloride → (3E)-4-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]but-3-en-2-ol

HRID 2078451Notes

Reaction equation

HRID 2078451 reaction equation
[CH:1]([O:4][C:5]1[CH:21]=[CH:20][C:8]([O:9][C:10]2[S:11][C:12](/[CH:15]=[CH:16]/[C:17](=[O:19])[CH3:18])=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO>[CH:1]([O:4][C:5]1[CH:21]=[CH:20][C:8]([O:9][C:10]2[S:11][C:12](/[CH:15]=[CH:16]/[CH:17]([OH:19])[CH3:18])=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 67096854(3E)-4-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]but-3-en-2-one

Product 1

HCID 67096817(3E)-4-[2-(4-isopropoxyphenoxy)-1,3-thiazol-5-yl]but-3-en-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of the product from Example 7C (1.4 g 4.6 mmole) in methanol (45 mL) at 0° C. was added a methanolic solution of 0.4 M cerium(III)chloride (13.8 mL, 5.5 mmole) followed by portion-wise addition of sodium borohydride (175 mg, 4.6 mmole). The reaction mixture was allowed to warm up to room temperature, stirred at room temperature for 15 minutes and quenched with acetone for 30 minutes. The reaction mixture was diluted with ethyl acetate and washed with water (×2) and brine. The reaction mixture was dried over magnesium sulfate filtered and evaporated. The crude product (1.4 g, quantitative) was carried on to the next step without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 1.32 (d, J=6.62 Hz, 3H) 1.34 (d, J=6.25 Hz, 6H) 1.56 (d, J=4.04 Hz, 1H) 4.33-4.46 (m, 1H) 4.47-4.59 (m, 1H) 5.82 (dd, J=15.63, 6.07 Hz, 1H) 6.56 (d, J=16.18 Hz, 1H) 6.83-6.97 (m, 2H) 7.05 (s, 1H) 7.11-7.22 (m, 2H). Mass spectrum DCI 306 (M+H)+.

Workup

  1. customquenched with acetone for 30 minutes
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washwashed with water (×2) and brine
  4. dry with materialThe reaction mixture was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product (1.4 g, quantitative) was carried on to the next step without further purification

Sources & evidence

ORD record
ord-66b1f14d4ee846688fd7922840e5e9c5
Source dataset
uspto-grants-2011_04
Patent number
US07928243B2

Reaction notes

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