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Triphenylphosphine → Ethyl 2-(3-(2-chloro-6-methylbenzyloxy)phenyl)acetate

HRID 516859
Notes
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Reaction equation

HRID 516859 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][OH:10].N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[C:26]1[CH:27]=[C:28]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:29]=[CH:30][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][O:10][C:30]1[CH:29]=[C:28]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:27]=[CH:26][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 572437Ethyl (3-Hydroxyphenyl)acetateHCID 20579023(2-Chloro-6-methylphenyl)methanol

Product 1

HCID 66875155Ethyl 2-(3-(2-chloro-6-methylbenzyloxy)phenyl)acetate

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2-chloro-6-methylphenyl)methanol (Step A, 3 g, 19.1 mmol) and diisopropyl azodicarboxylate (DIAD, 4.13 ml, 21 mmol) in THF (20 ml) was added drop wise to a solution of ethyl 2-(3-hydroxyphenyl)acetate (3.79 g, 21 mmol) and triphenylphosphine (5.48 g, 21 mmol) in THF (30 ml) at 0° C. under argon. 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, 2:1) 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, 2:1)

Sources & evidence

ORD record
ord-55f8c20bbe4e4aa699ede7ef7c7bb7fb
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09115072B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes