Dimethylformamide → HCID 14722832, compound

HRID 478022Notes

Reaction equation

HRID 478022 reaction equation
I[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:15]([CH2:16][CH2:17][CH3:18])=[C:14]2[C:9]([CH2:10][CH2:11][CH:12]([C:19]([O:21][CH3:22])=[O:20])[O:13]2)=[CH:8][CH:7]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].CN([CH:32]=[O:33])C>>[C:6]([C:7]1[CH:8]=[CH:9][C:32]([O:33][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[CH2:10][CH2:11][CH:12]([C:19]([O:21][CH3:22])=[O:20])[O:13][C:14]=3[C:15]=2[CH2:16][CH2:17][CH3:18])=[C:19]([CH2:12][CH:11]=[CH2:10])[C:23]=1[OH:26])(=[O:5])[CH3:15]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14722828HCID 14722828, compound

Product 1

HCID 14722832HCID 14722832, compound

Procedure

2,4-Dihydroxy-3-(2-propenyl) acetophenone (Aldrich, 12.5 g, 65 mMol) and methyl 7-(3-iodopropoxy)-8-propylchroman-2-carboxylate (29.9 g, 71.5 mMol) were dissolved in DMF (300 ml) containing powdered potassium carbonate (26.91 g, 195 mMol). The mixture was allowed to stir at room temperature under nitrogen for 8 hours and then partitioned between water and toluene. The organic layer was separated and washed with water and brine and then dried over sodium sulfate. Evaporation of the volatiles in vacuo afforded 36 g of crude product which was chromatographed on Merck 60 silica gel using 5:95 ethyl acetate/toluene as eluant. 25 g of pure methyl 7-[3-[4-acetyl-3-hydroxy-2-(2-propenyl)phenoxy]propoxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate were obtained in this manner.

Workup

  1. custompartitioned between water and toluene
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the volatiles in vacuo
  6. customafforded 36 g of crude product which
  7. customwas chromatographed on Merck 60 silica gel using 5:95 ethyl acetate/toluene as eluant

Sources & evidence

ORD record
ord-a4b5968027e8473899b11d43094bc477
Source dataset
uspto-grants-1989_12
Patent number
US04889871

Reaction notes

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