Sodium Bicarbonate → HCID 66777774, compound

HRID 2091271Notes

Reaction equation

HRID 2091271 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](OC)=[O:11])=[C:7]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:6]=2[CH:20]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:6]=2[CH:20]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 66779368HCID 66779368, compound

Product 1

HCID 66777774HCID 66777774, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 5-fluoro-3-[(2-methoxyethoxy)methyl]-1-benzofuran-2-carboxylate (1.54 g) synthesized above, calcium chloride (1.21 g), ethanol (15 mL) and tetrahydrofuran (15 mL) was added sodium borohydride (825 mg) at 0° C., and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (1.34 g, 97%) as a pale-yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4f378d55a354b2f96c82cbc8598a37f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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