Potassium Hydroxide → (E)-Parinaric acid

HRID 1050933Notes

Reaction equation

HRID 1050933 reaction equation
CO[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:28]C)[C:8]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1P(C1CCCCC1)C1CCCCC1.[OH-:30].[K+]>>[CH3:6][CH2:7]/[CH:8]=[CH:3]/[CH:4]=[CH:5]/[CH:14]=[CH:13]/[CH:12]=[CH:11]/[CH2:10][CH2:9][CH2:8][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:28])=[O:30]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 5282838(E)-Parinaric acid

Procedure

The machine was equipped with a deprotection tube (empty, but used for sparging the MIDA boronate solution) and a reaction tube charged with the Pd-mixture (60 mg), the SPhos-mixture (60 mg), KOH (75 mg, 1.7 mmol) and halide 3 (11 mg, 0.037 mmol).

Workup

  1. customThe machine was equipped with a deprotection tube (empty, but
  2. customfor sparging the MIDA boronate solution) and a reaction tube
  3. additioncharged with the Pd-mixture (60 mg)

Sources & evidence

ORD record
ord-5f6615cba0844fea9229613c7cd3b157
Source dataset
uspto-grants-2016_07
Patent number
US09388131B2

Reaction notes

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