Ethanol → HCID 59288328, compound

HRID 2420639Notes

Reaction equation

HRID 2420639 reaction equation
[H-].[K+].[Br:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([CH2:11][CH:12]([C:15]2[CH:24]=[C:23]3[C:18]([CH2:19][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:21][O:22]3)=[CH:17][C:16]=2[F:28])[CH2:13][OH:14])=[C:6](F)[CH:5]=1.C(O)C>C1COCC1.CCOCC>[Br:3][C:4]1[CH:5]=[C:6]2[C:7]([CH2:11][CH:12]([C:15]3[CH:24]=[C:23]4[C:18]([CH2:19][CH:20]([CH2:25][CH2:26][CH3:27])[CH2:21][O:22]4)=[CH:17][C:16]=3[F:28])[CH2:13][O:14]2)=[CH:8][C:9]=1[F:10]

Participants

6

Reactant 3

HCID 702EthanolHCID 82127Potassium hydrideHCID 59288335HCID 59288335, compound

Product 1

HCID 59288328HCID 59288328, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

1.2 g (10.5 mmol) of potassium hydride (35 percent in paraffin oil) are initially introduced in 40 ml of THF, and a solution of 4.50 g (8.12 mmol) of 3-(4-bromo-2,5-difluorophenyl)-2-(6-fluoro-3-propylchroman-7-yl)propan-1-ol in 20 ml of THF is added dropwise at 30° C. The batch is subsequently stirred at 60° C. for 4 h, a little ethanol is added, and the batch is diluted with MTB ether and washed with sat. sodium chloride soln. The org. phase is dried over sodium sulfate, the solvent is removed in vacuo, and the crude product is filtered through silica gel with toluene and recrystallised from heptane/ethyl acetate, giving 7-bromo-6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7′]-bichromenyl as colourless crystals.

Workup

  1. washwashed with sat. sodium chloride soln
  2. dry with materialphase is dried over sodium sulfate
  3. customthe solvent is removed in vacuo
  4. filtrationthe crude product is filtered through silica gel with toluene
  5. customrecrystallised from heptane/ethyl acetate

Sources & evidence

ORD record
ord-13518cb5df374d488085f5a455bfc6b3
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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