Ammonium Chloride → (2,3-Dihydro-1-benzofuran-7-yl)methanol

HRID 1363667Notes

Reaction equation

HRID 1363667 reaction equation
[O:1]1[C:5]2[C:6]([CH:10]=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[BH4-].[Na+].[Cl-].[NH4+]>CCOCC.CO>[O:1]1[C:5]2[C:6]([CH2:10][OH:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 27950182,3-Dihydro-1-benzofuran-7-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2795020(2,3-Dihydro-1-benzofuran-7-yl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2,3-Dihydro-benzofuran-7-carbaldehyde (1.50 g, 10.20 mmol) was dissolved in ether, then cooled to 0° C., NaBH4 (400 mg, 10.57 mmol) in MeOH (5.00 mL) was added. The resulting reaction mixture was stirred for 30 min, then saturated ammonium chloride was added. The mixture was extracted with ether, and the combined organic phases were washed with brine, then dried over magnesium sulfate and concentrated to afford the desired alcohol.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe mixture was extracted with ether
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3de0f6cb22b94ecfbc20de4fa8479d92
Source dataset
uspto-grants-2011_02
Patent number
US07884244B2

Reaction notes

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