Ammonium Chloride → 3-Ethynylbenzenemethanol

HRID 720117Notes

Reaction equation

HRID 720117 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])(C)C.[F-].[K+].[BH4-].[Na+].[NH4+].[Cl-]>CO>[C:6]([C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[CH:13][CH:14]=1)#[CH:5]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 522689Potassium FluorideHCID 27716423-(Trimethylsilyl)ethynylbenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 154687703-Ethynylbenzenemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

To 3-trimethylsilanylethynyl-benzaldehyde 73(a1) from step 1a in methanol (540 mL, 0.3 M) was added KF (18.8 g, 324 mmol), and the resulting mixture stirred at 22° C. for 6 hours. After cooling to 0° C., NaBH4 (6.13 g, 162 mmol) was carefully added over 0.5 hours. Aqueous saturated NH4Cl was carefully added and the volatiles were removed in vacuo. Ethyl acetate (200 mL) was added, and the organic phase was washed with water and a saturated aqueous NaCl solution, dried over MgSO4 and filtered. The volatiles were removed in vacuo to afford crude (3-ethynyl-phenyl)-methanol 73(a2).

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe volatiles were removed in vacuo
  3. additionEthyl acetate (200 mL) was added
  4. washthe organic phase was washed with water
  5. dry with materiala saturated aqueous NaCl solution, dried over MgSO4
  6. filtrationfiltered
  7. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-e870517df16449a9a7a25d74ab0bece6
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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