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Triphenylphosphine → HCID 66906418, compound

HRID 709578
Notes
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Reaction equation

HRID 709578 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].[F:16][C:17]1[C:25]2[CH:24]=[C:23]([CH2:26]O)[S:22][C:21]=2[CH:20]=[CH:19][CH:18]=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][CH2:26][C:23]2[S:22][C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([F:16])[C:25]=3[CH:24]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 12223651Dimethyl 3-hydroxyphthalateHCID 53396439(4-Fluoro-1-benzothiophen-2-yl)methanol

Product 1

HCID 66906418HCID 66906418, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.1 g, 5.2 mmol), (4-fluoro-benzo[b]thiophen-2-yl)-methanol (0.96 g, 10.5 mmol), and polymer-supported triphenyl phosphine (3.0 g, 10.5 mmol) in THF (35 mL) in an ice-bath was slowly added diisopropyl azodicarboxylate (2.1 mL, 10.5 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-(4-fluoro-benzo[b]thiophen-2-ylmethoxy)-phthalic acid dimethyl ester (1.5 g, 76% 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-93351b95db5948ce9630b56055e82ad8
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181216B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes