Triphenylphosphine → HCID 71533927, compound

HRID 1430770Notes

Reaction equation

HRID 1430770 reaction equation
[C:1]12([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:18]([O:22][CH3:23])(=[O:21])[C:19]#[CH:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1>[CH3:23][O:22][C:18](=[O:21])/[CH:19]=[CH:20]/[O:17][C:14]1[CH:13]=[CH:12][C:11]([C:1]23[CH2:8][CH:7]4[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]4)[CH2:10]2)[CH2:2]3)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 13536Methyl propiolateHCID 2699334-(1-Adamantyl)phenol

Product 1

HCID 71533927HCID 71533927, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

4-(Adamantan-1-yl)-phenol (1.0 mg, 4.38 mmol) and methyl propiolate (737 mg, 0.74 ml, 8.76 mmol) were dissolved in 25 ml of toluene, to which Ph3P (1.15 g, 4.38 mmol) was added, followed by reflux at 115° C. for 3 hours. The reaction solution was concentrated and extracted with EtoAC and NaCl solution. The organic layer was dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (n-Hexane:EtOAc=50:1) to give the target compound as a white solid (1.24 g, yield: 90.6%).

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated
  3. extractionextracted with EtoAC and NaCl solution
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-Hexane:EtOAc=50:1)

Sources & evidence

ORD record
ord-9771530ec8ad4ea682a76ac7bdd5e4c9
Source dataset
uspto-grants-2015_01
Patent number
US08940936B2

Reaction notes

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