Methanol → HCID 22630961, compound

HRID 2416532Notes

Reaction equation

HRID 2416532 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[CH:15]=[O:16])=[CH:9][CH:8]=1.CO.[BH4-].[Na+]>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[CH2:15][OH:16])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 22630962(E)-3-[4-(2-Pyridinyl)phenyl]-2-propenal

Product 1

HCID 22630961HCID 22630961, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(2E)-3-[4-(2-pyridinyl)phenyl]-2-propenal (500 mg, 2.4 mmol, prepared as described in Reference Example 32) was dissolved in THF (10 mL) and methanol (10 mL) at 0° C. Sodium borohydride (109 mg, 2.9 mmol) was added and the mixture was stirred at 0° C. for 30 min. The reaction mixture was concentrated. Water (10 mL) was added and the mixture was extracted with ethyl acetate (3×15 mL). The organic layer was collected, dried and concentrated. MS 212 (M+H)+.

Workup

  1. customat 0° C
  2. concentrationThe reaction mixture was concentrated
  3. additionWater (10 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (3×15 mL)
  5. customThe organic layer was collected
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e676a09973cc46edada32e6b1332a178
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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