Triphenylphosphine → HCID 66906475, compound

HRID 709575Notes

Reaction equation

HRID 709575 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[C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[S:20][C:21]=1[CH2:22]O.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][CH2:22][C:21]2[S:20][C:19]3[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=3[C:17]=2[Cl:16])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 821965(3-Chloro-1-benzothien-2-yl)methanolHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 66906475HCID 66906475, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.0 g, 4.8 mmol), (3-chloro-benzo[b]thiophen-2-yl)-methanol (1.9 g, 9.5 mmol), and polymer-supported triphenyl phosphine (3.0 g, 9.5 mmol) in THF (30 mL) in an ice-bath was slowly added diisopropyl azodicarboxylate (1.9 mL, 9.5 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-chloro-benzo[b]thiophen-2-ylmethoxy)-phthalic acid dimethyl ester (2.1 g, 109% crude 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-2ba7eee4d1344840b2911fe98e6629e2
Source dataset
uspto-grants-2015_11
Patent number
US09181216B2

Reaction notes

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