Water → HCID 86621970, compound

HRID 2422506Notes

Reaction equation

HRID 2422506 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18](O)=[O:19])=[CH:15][CH:16]=3)[O:11][C:10](=[O:21])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[BH4-].[Na+].O.[Cl-].[NH4+]>C1COCC1>[OH:19][CH2:18][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)=[CH:9][C:10](=[O:21])[O:11]2)=[CH:16][CH:15]=1

Participants

8

Reactant 6

HCID 962WaterHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 86621968HCID 86621968, compound

Product 1

HCID 86621970HCID 86621970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-methylphenyl)-2-oxo-2H-chromene-7-carboxylic acid (520 mg, 1.86 mmol) and triethylamine (1.0 mL, 7.4 mmol) in THF (15 mL), cooled at 0° C., isobutylchloroformate (726 uL, 5.6 mmol) was added dropwise. After 1 hour stirring at 0° C. a solution of sodium borohydride in water (353 mg, 9.3 mmol in 6 mL) was added slowly and the mixture was stirred for another hour. The reaction mixture was poured into a saturated ammonium chloride solution and the product was extracted (3×) with ethyl acetate, the combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue obtained was purified by column chromatography (ethyl acetate/hexanes, 50:50) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 7.51-7.39 (m, 5H), 7.37 (d, 1H), 7.32 (d, 1H), 6.29 (s, 1H), 4.79 (d, 2H), 4.57 (t, 1H), 2.46 (s, 3H).

Workup

  1. additionwas added slowly
  2. extractionthe product was extracted (3×) with ethyl acetate
  3. washthe combined organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue obtained
  8. customwas purified by column chromatography (ethyl acetate/hexanes, 50:50)

Sources & evidence

ORD record
ord-8f4c9c9d194e48b0b85139a0ffc7a88a
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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