Sodium borohydride → HCID 21959212, compound

HRID 2055046Notes

Reaction equation

HRID 2055046 reaction equation
[BH4-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[CH:10]=[CH:9][C:8]=1[C:17]1[C:18](=[O:34])[O:19][C:20]2[C:25]([C:26]=1[CH2:27][CH:28]=[O:29])=[CH:24][CH:23]=[C:22]([O:30][CH2:31][O:32][CH3:33])[CH:21]=2>C(O)C>[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[CH:10]=[CH:9][C:8]=1[C:17]1[C:18](=[O:34])[O:19][C:20]2[C:25]([C:26]=1[CH2:27][CH2:28][OH:29])=[CH:24][CH:23]=[C:22]([O:30][CH2:31][O:32][CH3:33])[CH:21]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21959222HCID 21959222, compound

Product 1

HCID 21959212HCID 21959212, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (17 mg, 0.45 mmol, 0.5 eq.) was dissolved in ethanol (5 mL), then added into the solution of [3-(2,4-Bis-methoxymethoxy-phenyl)-7-methoxymethoxy-2-oxo-2H-chromen-4-yl]-acetaldehyde (400 mg, 0.90 mmol, 1 eq.) ethanol (10 mL) at −10° C. and the reaction mixture was stirred for 30 minutes. The solvent was evaporated and the resulting residue was dissolved in ethyl acetate (100 mL) and washed twice with brine. The organic layer was dried over anhydrous sodium sulfate then concentrated to yield the crude product which was purified by flash chromatography eluted with 50% ethyl acetate to yield the title compound 3-(2,4-Bis-methoxymethoxy-phenyl)-4-(2-hydroxy-ethyl)-7-methoxymethoxy-chromen-2-one as a solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting residue was dissolved in ethyl acetate (100 mL)
  3. washwashed twice with brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationthen concentrated
  6. customto yield the crude product which
  7. customwas purified by flash chromatography
  8. washeluted with 50% ethyl acetate

Sources & evidence

ORD record
ord-228e3ed850514ab1b809e9d79d795bfa
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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