Triphenylphosphine → HCID 66874946, compound

HRID 516856Notes

Reaction equation

HRID 516856 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][OH:5].N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[C:26]1[CH:27]=[C:28]([C:32]2([C:35]#[N:36])[CH2:34][CH2:33]2)[CH:29]=[CH:30][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOCC>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][O:5][C:26]1[CH:27]=[C:28]([C:32]2([C:35]#[N:36])[CH2:33][CH2:34]2)[CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 186748(2,6-Dimethylphenyl)methanolHCID 66875026940307-96-0

Product 1

HCID 66874946HCID 66874946, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,6-Dimethylbenzyl alcohol (2.81 g, 20.6 mmol) and diisopropyl azodicarboxylate (DIAD, 4.69 g, 23.2 mmol) in THF (20 ml) was added drop wise to a solution of 1-(3-hydroxyphenyl)cyclopropanecarbonitrile (Step B, 3.2 g, 20.1 mmol) and triphenylphosphine (5.37 g, 20.5 mmol) in THF (50 ml) at 0° C. under argon. The reaction mixture was stirred at the same temperature for 16 hours, diluted with ether and washed with water. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate, 9:1) to give the title compound.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-1cc15a072a704824961fea3cd3383823
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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