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Triphenylphosphine → 1-Acetyl-6-bromo-2,3-dihydro-5-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)methoxy-1H-indole

HRID 1741028
Notes
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Reaction equation

HRID 1741028 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[O:15]1[C:19]2([CH2:24][CH2:23][C:22]([CH2:25]O)=[CH:21][CH2:20]2)[O:18][CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(OCC)(=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH2:25][C:22]3[CH2:23][CH2:24][C:19]4([O:15][CH2:16][CH2:17][O:18]4)[CH2:20][CH:21]=3)=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 109649381,4-Dioxaspiro[4.5]dec-7-en-8-ylmethanolHCID 219483801-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 218345511-Acetyl-6-bromo-2,3-dihydro-5-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)methoxy-1H-indoleYield 180.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Acetyl-6-bromo-2,3-dihydro-1H-indol-5-ol (Tetrahedron 1973, 29, 1115) (1.10 g, 4.3 mmol), 1,4-dioxaspiro[4,5]dec-7-ene-8-methanol (D11, 0.88 g, 5.2 mmol) and triphenylphosphine (1.36 g, 5.2 mmol) were stirred under Ar in dry THF (50 ml) as diethyl azodicarboxylate (0.82 ml, 5.2 mmol) was added dropwise. The mixture was stirred for 1 h, diluted with ethyl acetate (100 ml), washed with brine, dried (Na2SO4) and evaporated to give a dark oil. Chromatography on silica gel, eluting with 0-5% methanol/dichloromethane, gave the title compound (3.17 g) contaminated by substantial amounts of triphenylphosphine and diethyl azodicarboxylate-derived residues (NMR).

Workup

  1. additionwas added dropwise
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give a dark oil
  6. washChromatography on silica gel, eluting with 0-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-5293d020eaf740ea927da12201f4305d
Source dataset
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05972979

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes