Triphenylphosphine → HCID 16662683, compound

HRID 1925235Notes

Reaction equation

HRID 1925235 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)=N[C:13](OC(C)C)=O.O[C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])[CH:29]=[CH:30][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CN(C=O)C.CCOCC>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][O:5][C:30]1[CH:29]=[C:28]([CH2:32][CH:33]([CH3:13])[C:34]([OH:36])=[O:35])[CH:27]=[CH:26][CH:31]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 186748(2,6-Dimethylphenyl)methanolHCID 15197885Ethyl 3-(3-hydroxyphenyl)propanoate

Product 1

HCID 16662683HCID 16662683, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,6-Dimethylbenzyl alcohol (7.71 g, 56.7 mmol) and diisopropyl azodicarboxylate (DIAD, 11.36 g, 56.18 mmol) in THF (30 ml) and DMF (13 ml) was added drop wise to a solution of Ethyl 3-(3-hydroxyphenyl)propanoate (Step A, 10.0 g, 51.5 mmol) and triphenylphosphine (14.73 g, 56.18 mmol) in THF (100 ml) at 0° C. The reaction mixture was stirred at the same temperature for 4 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 4:1) 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 4:1)

Sources & evidence

ORD record
ord-54ff6af00b2b48a4aaac2b1dc106a1a1
Source dataset
uspto-grants-2012_05
Patent number
US08178675B2

Reaction notes

Loading…