Sodium Bicarbonate → 1-(7-Hydroxymethyl-benzofuran-5-yl)-ethanone

HRID 1584776Notes

Reaction equation

HRID 1584776 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:13]=[O:14])[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)(=[O:3])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[OH:14][CH2:13][C:6]1[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21220947HCID 21220947, compound

Product 1

HCID 212208891-(7-Hydroxymethyl-benzofuran-5-yl)-ethanoneYield 57.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-acetyl-benzofuran-7-carbaldehyde (471 mg) in dry toluene (40 ml) was treated with sodium triacetoxyborohydride (1.12 ml) and heated at reflux for 5.5 h. The reaction mixture was poured into 8% sodium bicarbonate (40 ml) and the phases were separated. The aqueous phase was extracted with ethyl acetate (40 ml), the combined organic phases were dried, filtered, and the filtrate evaporated in vacuo to give a yellow gum. Purification by FCC eluted with hexane:ethyl acetate (2:1→1:1) gave the title compound as a pale yellow oil (275 mg) which slowly solidified.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5.5 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (40 ml)
  5. customthe combined organic phases were dried
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customto give a yellow gum
  9. customPurification by FCC
  10. washeluted with hexane:ethyl acetate (2:1→1:1)

Sources & evidence

ORD record
ord-708bb31745db4974a2a603adb9bad6f2
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

Loading…