Triphenylphosphine → HCID 66906348, compound

HRID 709549Notes

Reaction equation

HRID 709549 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[Cl:16][C:17]1[CH:18]=[C:19]([CH2:24]O)[CH:20]=[C:21]([Cl:23])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([O:14][CH2:24][C:19]2[CH:18]=[C:17]([Cl:16])[CH:22]=[C:21]([Cl:23])[CH:20]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 432363,5-Dichlorobenzylic alcoholHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 66906348HCID 66906348, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (0.5 g, 2.4 mmol), (3,5-dichloro-phenyl)-methanol (0.84 g, 4.8 mmol), and polymer-supported triphenyl phosphine (1.5 g, 4.8 mmol) in THF (30 mL) in ice-bath was slowly added diisopropyl azodicarboxylate (1.0 mL, 4.8 mmol) and stirred at r.t. overnight. The mixture was filtered and the solid was washed with ethyl acetate (10 mL). The filtrate was evaporated and the residue was purified by flash column chromatography (EtOAc/Hexane) to give 3-(3,5-dichloro-benzyloxy)-phthalic acid dimethyl ester (0.42 g, 48% yield). The product was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with ethyl acetate (10 mL)
  3. customThe filtrate was evaporated
  4. customthe residue was purified by flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-ddfaf7154ebb49599f37550af7644906
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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