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Potassium Phosphate, Tribasic → (1RS,2RS,6-SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]dec-4-en-3-one

HRID 407841
Notes
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Reaction equation

HRID 407841 reaction equation
Br[C:2]1[C:3](=[O:14])[CH:4]2[CH:9]([C:10]=1[O:11][CH3:12])[CH:8]1[O:13][CH:5]2[CH2:6][CH2:7]1.[CH2:15]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH2:24][CH3:25])[C:18]=1B(O)O)[CH3:16].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:24]([C:19]1[CH:20]=[C:21]([CH3:23])[CH:22]=[C:17]([CH2:15][CH3:16])[C:18]=1[C:2]1[C:3](=[O:14])[CH:4]2[CH:9]([C:10]=1[O:11][CH3:12])[CH:8]1[O:13][CH:5]2[CH2:6][CH2:7]1)[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57437319(2,6-Diethyl-4-methylphenyl)boronic acidHCID 67283643(1RS, 2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one

Product 1

HCID 67283587(1RS,2RS,6-SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]dec-4-en-3-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (1RS, 2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one (0.315 g, 1.2 mmol), 2,6-diethyl-4-methylphenylboronic acid (0.35 g, 1.8 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (20 mg, 0.048 mmol), palladium (II)acetate (5.5 mg, 0.024 mmol) and potassium phosphate (0.51 g, 2.4 mmol) are heated in degassed toluene at 95° C. for 24 hours. The reaction mixture is partitioned between dichloromethane and water, and the organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one.

Workup

  1. customThe reaction mixture is partitioned between dichloromethane and water
  2. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe filtrate is evaporated under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-28a0ed9137cb4c26adbcd8b734595c72
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754242B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes