Sodium borohydride → HCID 58934493, compound

HRID 855050Notes

Reaction equation

HRID 855050 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][CH:14]=1)[O:8][CH:7]([C:21]([F:24])([F:23])[F:22])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2.[BH4-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=1)[O:8][CH:7]([C:21]([F:24])([F:22])[F:23])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58934884HCID 58934884, compound

Product 1

HCID 58934493HCID 58934493, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The 6-chloro-7-(4-formylbenzyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid (Example 604 g) (210 mg, 0.49 mmole) was dissolved in MeOH:THF (1:1) (3 mL). NaBH4 (20 mg, 0.49 mmole) was added to the above solution portionwise. After stiring for 15 min, the reaction was finished. The reaction was quenched with (sat.) NH4Cl, the organic layer was extracted with EtOAc and dried over MgSO4 and filtered. The filtrate was concentrated to give the title compound as an oil, which solidify upon standing as a white solid 200 mg (95% yield): ESHRMS m/z 397.0457 (M−H, C19H13O4F3Cl, Calc'd 397.0449). 1H NMR (acetone-d6/400 MHz) 7.87 (s, 1H), 7.57 (s, 1H), 7.31 (d, 2H, J=8.2 Hz), 7.22 (d, 2H, J=8.2 Hz), 6.92 (s, 1H), 5.80 (q, 1H, J=7.2 Hz), 4.59 (s, 2H), 4.09 (d, 2H, J=4.3 Hz).

Workup

  1. customThe reaction was quenched with (sat.) NH4Cl
  2. extractionthe organic layer was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d0fda0c3bf1a46d7ac6ca941c5ea57b0
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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