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Triphenylphosphine → 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-2,2-dimethyl-propionic acid methyl ester

HRID 20761
Notes
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Reaction equation

HRID 20761 reaction equation
[OH:1][CH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].O[C:11]1[CH:21]=[CH:20][CH:19]=[C:13]2[C:14]([NH:16][C:17](=[O:18])[C:12]=12)=[O:15].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>O1CCCC1>[CH3:7][O:6][C:4](=[O:5])[C:3]([CH3:9])([CH3:8])[CH2:2][O:1][N:16]1[C:17](=[O:18])[C:12]2[C:13](=[CH:19][CH:20]=[CH:21][CH:11]=2)[C:14]1=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 84152Methyl 3-hydroxypivalateHCID 3460024-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 593480263-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-2,2-dimethyl-propionic acid methyl esterYield 33.6%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To methyl hydroxypivalate (1.31 g, 9.89 mmol) were added tetrahydrofuran (40 ml), hydroxyphthalimide (3.23 g, 19.78 mmol) and triphenylphosphine (6.48 g, 24.73 mmol). After this solution was cooled to 0° C., diisopropyl azodicarboxylate (4.87 ml, 24.73 mmol) was added dropwise to the solution. While being allowed to warm gradually, the reaction mixture was stirred for 12 hours, and concentrated under reduced pressure. The residue was roughly purified by silica gel column chromatography to give the title compound (922 mg).

Workup

  1. temperatureto warm gradually
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was roughly purified by silica gel column chromatography

Sources & evidence

ORD record
ord-97c9716f95c14692a5ef32b3dbd750ba
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745663B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes