Triphenylphosphine → Ethyl 3-(2,6-dimethylbenzyloxy)-4-methoxybenzoate

HRID 337248Notes

Reaction equation

HRID 337248 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:29][C:30]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:31]=1[CH2:32]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:29][C:30]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:31]=1[CH2:32][O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 186748(2,6-Dimethylphenyl)methanolHCID 15480330Ethyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 66692649Ethyl 3-(2,6-dimethylbenzyloxy)-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Ethyl 3-hydroxy-4-methoxybenzoate (Step A, 9.10 g, 46.4 mmol) and diisopropyl azodicarboxylate (DIAD, 10.23 g, 50 mmol) in dry THF (20 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (6.94 g, 51 mmol) and triphenylphosphine (TPP, 13.27 g, 50 mmol) in dry THF (60 ml) at 0° C. under argon. The reaction mixture was warmed to room temperature for 4 hours or until all the starting material is consumed, diluted with ether and washed with water (2×). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound.

Workup

  1. customis consumed
  2. additiondiluted with ether
  3. washwashed with water (2×)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

Sources & evidence

ORD record
ord-56528b951d114edd851b3b9ffe94c412
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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