Sodium borohydride → HCID 22291332, compound

HRID 967759Notes

Reaction equation

HRID 967759 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[N:13]=[C:12]([C:14](OCC)=[O:15])[S:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1(/[CH:7]=[CH:8]/[C:9]2[N:13]=[C:12]([CH2:14][OH:15])[S:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13021999HCID 13021999, compound

Product 1

HCID 22291332HCID 22291332, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-[(E)-2-phenylethenyl]-1,2,4-thiadiazole-5-carboxylate (1.0 g, 3.8 mmol) was suspended in methanol (50 mL), and NaBH4 (220 mg, 5.8 mmol) was added in portions. The mixture was stirred for 16 h at ambient temperature. The reaction was concentrated in vacuo, acidified with aqueous HCl (4 M) to pH 2, and partitioned between Ethyl acetate and water. The organics were dried over Na2SO4, concentrated in vacuo, and the resultant material was rerystallized from ethyl acetate to afford {3-[(E)-2-phenylethenyl]-1,2,4-thiadiazol-5-yl}methanol (0.6 g, 71% yield) as a pale yellow solid. M.p. 119–120° C. 1H NMR (CDCl3, 300 MHz) δ 7.79 (d, J=16 Hz, 1H), 7.57 (m, 2H), 7.38 (m, 3H), 7.23 (d, J=16 Hz, 1H), 5.14 (d, J=5 Hz, 2H), 3.29 (t, J=5 Hz, 1H). MS (EI ionization) 217 (M+−H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between Ethyl acetate and water
  3. dry with materialThe organics were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5ecb6a82a134edc8fb1d8352c06b819
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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