1,2-Dimethoxyethane → HCID 58687492, compound

HRID 2052773Notes

Reaction equation

HRID 2052773 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([F:19])=[C:17]2[C:12]([C:13]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[C:21]([F:28])[C:14]=3[C:15](=O)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1C=CC(OCC)=C(F)C=1.COCCOC.[BH4-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[C:18]([F:19])=[C:17]2[C:12]([C:13]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[C:21]([F:28])[C:14]=3[CH2:15][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 4311764Sodium borohydrideHCID 145169324-Bromo-1-ethoxy-2-fluorobenzeneHCID 58687478HCID 58687478, compound

Product 1

HCID 58687492HCID 58687492, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.00 g (5.24 mmol) of 3-benzyloxy-8-ethoxy-4,7-difluoro-6H-benzo[c]chromen-6-one, the compound of Example 841, were dissolved in 12 ml of THF, and 2.37 ml (23.0 mmol) of boron trifluoride/THF complex were added with ice-cooling. 24 ml of ethylene glycol dimethyl ether and then in portions 530 mg of sodium borohydride were subsequently added. The mixture was subsequently stirred at room temperature for 18 hours and then transferred onto ice. The mixture was subjected to conventional purification, giving 1.5 g (78% of theory) of 3-benzyloxy-8-ethoxy-4,7-difluoro-6H-benzo[c]chromene as colourless crystals. These were dissolved in THF, hydrogenated at a pressure of 1 bar in the presence of 0.6 g of Pd/C (5%), filtered and evaporated, giving 1.2 g (99% of theory) of 8-ethoxy-4,7-difluoro-3-hydroxy-6H-benzo[c]chromene as colourless crystals.

Workup

  1. addition2.37 ml (23.0 mmol) of boron trifluoride/THF complex were added with ice-
  2. temperaturecooling
  3. customThe mixture was subjected to conventional purification

Sources & evidence

ORD record
ord-d9d2b166268e4873bc3cf52972636693
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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