Hydrochloric Acid → HCID 69517865, compound

HRID 855108Notes

Reaction equation

HRID 855108 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:13])[CH:12]=1)[O:9][CH:8]([C:14]([F:17])([F:16])[F:15])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6]2)=[O:2].[BH4-].[Na+].Cl>C1COCC1.C(O)C>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([CH3:13])[CH:12]=1)[O:9][CH:8]([C:14]([F:16])([F:17])[F:15])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86599489HCID 86599489, compound

Product 1

HCID 69517865HCID 69517865, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The solution of ethyl 6-formyl-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate (1.9 g, 6.05 mmole) dissolved in a mixture of THF (10 mL) and ethanol (10 mL) was cooled to 0° C. (ice bath). Sodium borohydride (0.11 g, 3.00 mmole) was added to above solution portionwise over 30 minutes. The mixture was poured into 1.2 N HCl (10 ml) and extracted with EtOAc (2×20 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil (1.9 g, 98%). No further purification was performed. GCMS m/z 316.0 (M+).

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined extracts were washed with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85ebd54cc23c4db79da5acb38804593e
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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