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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
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HRID 1741028 반응식
[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]
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5293d020eaf740ea927da12201f4305d
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05972979

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