Water → 3-[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl]propanol

HRID 1604636Notes

Reaction equation

HRID 1604636 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[N:12]=[C:13]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](OCC)=[O:28])=[CH:21][C:19]=3[CH:20]=2)[S:14][CH:15]=1)([CH3:10])([CH3:9])[CH3:8].O>O1CCCC1>[C:7]([C:11]1[N:12]=[C:13]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:21][C:19]=3[CH:20]=2)[S:14][CH:15]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 19603662Ethyl 3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propionateHCID 21226445Aluminium lithium hydride

Product 1

HCID 196037673-[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl]propanolYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.14 g) was added to a solution of ethyl 3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propionate (0.65 g) in tetrahydrofuran (10 ml) at room temperature under an inert atmosphere. After the mixture was stirred for 2 hours, water was added to the mixture. The resulting precipitates were filtered off and the filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 3-[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]propanol (0.42 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere filtered off
  3. extractionthe filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0d9653e011b491d9e2f28933dd81c28
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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