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Water → HCID 11591698, compound

HRID 2076601
Notes
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Reaction equation

HRID 2076601 reaction equation
N1CCOCC1.C([O:10][C:11]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[C:20]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([CH2:42][C:43]([O:45]CC=C)=[O:44])=[C:38]([F:49])[CH:37]=3)=[CH:32][CH:31]=2)[C:12]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])C=C.O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([O:15][C:13]([C:12]1[C:11]([OH:10])=[C:23]([C:24]([F:27])([F:25])[F:26])[CH:22]=[CH:21][C:20]=1[CH2:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42][C:43]([OH:45])=[O:44])=[C:38]([F:49])[CH:37]=2)=[CH:34][CH:35]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 67119033HCID 67119033, compound

Product 1

HCID 11591698HCID 11591698, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

Morpholine (0.27 ml, 3.3 mmol) and tetrakis(triphenylphosphine)palladium (0) (57 mg, 0.049 mmol) were successively added to a solution of tert-butyl 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (790 mg, 1.32 mmol) obtained in Example (11-6) in tetrahydrofuran (8 ml), and the mixture was stirred at room temperature for 1 hour. After water was poured into the reaction mixture and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. After the residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1-0/1), it was crystallized from a mixture solvent of methylene chloride-ethyl acetate to give the title compound as a colorless powder (323 mg, yield: 47%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customAfter the residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1-0/1), it
  7. customwas crystallized from a mixture solvent of methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-ed32fbd9a7a54ceeb0d2229050f364fb
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07923573B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes