Sodium metaborate → HCID 57552324, compound

HRID 1169543Notes

Reaction equation

HRID 1169543 reaction equation
[CH2:1]([CH:4]1[CH2:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7](OS(C(F)(F)F)(=O)=O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=C(OCOCCOC)[C:26]=1[F:41])[CH3:23].B([O-])=O.[Na+].[OH-].[NH3+]N>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:22]([O:24][C:25]1[C:26]([F:41])=[C:13]2[C:28]([C:7]3[CH2:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:9][C:8]=3[C:10](=[O:11])[O:12]2)=[CH:29][CH:30]=1)[CH3:23]

Participants

8

Reactant 4

HCID 145326Sodium metaborateHCID 44558531Aminoammonium hydroxideHCID 57552323HCID 57552323, compoundHCID 57552327HCID 57552327, compound

Product 1

HCID 57552324HCID 57552324, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

18.2 g (56.6 mmol) of methyl 5-propyl-2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate, 21.5 g (74.6 mmol) of 4-ethoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzeneboronic acid, 1.5 ml of water, 33 g (120 mmol) of sodium metaborate, 1.12 g (1.6 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.1 ml (1.6 mmol) of hydrazinium hydroxide are heated under reflux overnight in 300 ml of tetrahydrofuran. After addition of water, the aqueous phase is separated off and extracted twice with MTB ether. The combined organic phases are washed with saturated sodium chloride soln. and dried over sodium sulfate. The solvent is removed under reduced pressure, and the residue is filtered through silica gel with n-heptane/MTB ether (6:4), giving 3-ethoxy-4-fluoro-8-propyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one as colourless crystals.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted twice with MTB ether
  3. washThe combined organic phases are washed with saturated sodium chloride soln
  4. dry with materialand dried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. filtrationthe residue is filtered through silica gel with n-heptane/MTB ether (6:4)

Sources & evidence

ORD record
ord-4a0d819ddab24527bb2cfaab3e96d396
Source dataset
uspto-grants-2010_11
Patent number
US07824745B2

Reaction notes

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