Triethylamine → HCID 57729259, compound

HRID 1988195Notes

Reaction equation

HRID 1988195 reaction equation
ClC(OCC(C)C)=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:27](O)=[O:28])=[C:23]([CH3:26])[CH:24]=3)[O:19][C:18](=[O:30])[CH:17]=2)=[CH:12][CH:11]=1.CCN(CC)CC.[BH4-].[Na+]>C1COCC1.O>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([CH2:27][OH:28])=[C:23]([CH3:26])[CH:24]=3)[O:19][C:18](=[O:30])[CH:17]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 57729249HCID 57729249, compound

Product 1

HCID 57729259HCID 57729259, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Isobutyl chloroformate (0.775 mL, 5.97 mmol) was added dropwise to 4-(4-fluorophenyl)-6-methyl-2-oxo-2H-chromene-7-carboxylic acid (0.594 g, 1.99 mmol) and Et3N (1.11 mL, 7.96 mmol) in THF (13 mL) at 0° C. After 1 h, a freshly prepared solution of NaBH4 0.377 g, 9.96 mmol) in water (10 mL) was added rapidly. The reaction mixture was stirred at 0° C. for 1 h, quenched using saturated. NH4Cl and extracted with EtOAc (3×). The combined organic extracts were washed with 1 N HCl, 5% NaHCO3 and brine, dried (Na2SO4) and concentrated. The residue was subjected to column chromatography on silica gel (EtOAc—CHCl3, 30:70, then 35:65, then 40:60) to afford the title compound. 1H NMR (400 MHz, acetone-d6): δ 7.65 (m, 2H), 7.53 (s, 1H), 7.38 (m, 2H), 7.26 (s, 1H), 6.30 (s, 1H), 4.76 (d, 2H), 4.55 (t, 1H), 2.26 (s, 3H).

Workup

  1. customquenched
  2. extractionNH4Cl and extracted with EtOAc (3×)
  3. washThe combined organic extracts were washed with 1 N HCl, 5% NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2e19c1c09fd240489fbfc3fd558a8eb5
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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