Triphenylphosphine → HCID 66906418, compound

HRID 1690466Notes

Reaction equation

HRID 1690466 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]

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 8028TetrahydrofuranSolvent

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-84c3a563a8e94db9857f4dd908622d86
Source dataset
uspto-grants-2012_04
Patent number
US08153659B2

Reaction notes

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