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Triphenylphosphine → 6-Allyl-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)3H-isobenzofuran-1-one

HRID 33665
Notes
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Reaction equation

HRID 33665 reaction equation
[CH2:1]([C:4]1[C:12]([OH:13])=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:14])=[C:6]([CH3:15])[C:5]=1[CH2:16][CH3:17])[CH:2]=[CH2:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:37][Si:38]([CH3:43])([CH3:42])[CH2:39][CH2:40]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:1]([C:4]1[C:12]([O:13][CH2:40][CH2:39][Si:38]([CH3:43])([CH3:42])[CH3:37])=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:14])=[C:6]([CH3:15])[C:5]=1[CH2:16][CH3:17])[CH:2]=[CH2:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 180132-(Trimethylsilyl)ethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 574598626-allyl-5-ethyl-7-hydroxy-4-methyl-3H-isobenzofuran-1-one

Product 1

HCID 574598636-Allyl-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)3H-isobenzofuran-1-oneYield 92%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-allyl-5-ethyl-7-hydroxy-4-methyl-3H-isobenzofuran-1-one (199 mg, 0.857 mmol), PPh3 (337 mg, 1.286 mmol), and 2-trimethylsilylethanol in THF (3 mL) at 0° C. was added diisopropyl azodicarboxylate (259 mg, 1.286 mmol). The resulting yellow solution was allowed to warm to room temperature and stirred for one hour. The solvent was removed in vacuo and the crude material was dissolved in diethyl ether (3 mL). Hexanes (1.5 mL) were added. Triphenylphosphine oxide was removed by filtration and the filtrate was concentrated and purified by silica gel chromatography to provide the desired product (261 mg, 92%) as a clear oil. 1H NMR (300 MHz, CDCl3): δ=0.04 (s, 9H), 1.15 (t, J=7.8 Hz, 3H), 1.25 (m, 2H), 2.20 (s, 3H), 2.73 (q, J=7.8 Hz, 2H), 3.54 (m, 2H), 4.28 (m, 2H), 4.95 (d, J=17.1 Hz, 1H), 5.02 (d, J=10.2 Hz, 1H), 5.15 (s, 2H), 5.95 (m, 1H) ppm.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude material was dissolved in diethyl ether (3 mL)
  3. additionHexanes (1.5 mL) were added
  4. customTriphenylphosphine oxide was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-5affdf2ab1d74a689fcc6a057efa0902
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429565B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes