2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehyde → (2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)methanol

HRID 1253229Notes

Reaction equation

HRID 1253229 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:15])[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([CH:13]=[O:14])[C:6]=2[O:5]1>C(O)C>[CH3:3][C:4]1([CH3:15])[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([CH2:13][OH:14])[C:6]=2[O:5]1

Participants

4

Reactant 2

HCID 27954712,2-Dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2795472(2,2-Dimethyl-2,3-dihydro-1-benzofuran-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.08 grams, 0.0285 mole) was added carefully in small portions to a stirred solution of 2,3-dihydro-2,2-dimethylbenzofuran-7-carboxaldehyde (10.0 grams, 0.057 mole) in ethanol (150 ml) at 5°-10° C. during a ten minute period. The reaction mixture was stirred for thirty minutes and was then quenched by the dropwise addition of water (25 ml) followed by 10% hydrochloric acid (25 ml). The reaction mixture was concentrated under reduced pressure leaving a residue. This residue was partitioned between diethyl ether (75 ml) and 10% hydrochloric acid (30 ml). The layers were separated, and the organic layer was washed with water (40 ml) and a saturated aqueous solution of sodium chloride (40 ml). The dried (sodium sulfate) organic solution was concentrated under reduced pressure, yielding 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethanol as a solid. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customwas then quenched by the dropwise addition of water (25 ml)
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customleaving a residue
  4. customThis residue was partitioned between diethyl ether (75 ml) and 10% hydrochloric acid (30 ml)
  5. customThe layers were separated
  6. washthe organic layer was washed with water (40 ml)
  7. dry with materialThe dried (sodium sulfate) organic solution
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae76aa1618574f12b160277ac1b3ac6d
Source dataset
uspto-grants-1988_05
Patent number
US04748186

Reaction notes

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