Triphenylphosphine → Ethyl 3-(2,6-dimethylbenzyloxy)benzoate

HRID 1820940Notes

Reaction equation

HRID 1820940 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][C:33]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:34]=1[CH2:35]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.CN(C=O)C.C(OCC)C>[CH3:32][C:33]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:34]=1[CH2:35][O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 24522Ethyl 3-hydroxybenzoateHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 186748(2,6-Dimethylphenyl)methanol

Product 1

HCID 10062422Ethyl 3-(2,6-dimethylbenzyloxy)benzoate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of Ethyl 3-hydroxybenzoate (12.21 g, 73.47 mmol) and triphenylphosphine (21.01 g, 80.13 mmol) in dry THF (100 ml) was added dropwise a solution of 2,6-Dimethylbenzyl alcohol (10 g, 73.5 mmol) and diisopropyl azodicarboxylate (16.19 g, 80.13 mmol) in dry THF (35 ml) and dry DMF (15 ml) at ambient temperature. After three hours of stirring at room temperature, the reaction mixture was diluted with diethyl ether and washed twice with water and brine. The combined organic layer was dried over Na2SO4, filtered, concentrated and purified by flash chromatography using ethyl acetate:hexane (1:3) as elutent.

Workup

  1. washwashed twice with water and brine
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-f049ce5977da48fcaa55c32306cfadd4
Source dataset
uspto-grants-2009_10
Patent number
US07605181B2

Reaction notes

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