Benzyl Alcohol → 6-(Benzyloxy)-2,3-dihydro-1H-inden-1-one

HRID 1720073Notes

Reaction equation

HRID 1720073 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:13]1([CH2:12][O:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][C:8]3=[O:11])=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 224199626-(Benzyloxy)-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-hydroxyindan-1-one (1.60 g, 10.8 mmol (M. Phialas, P. G. Sammes, P. D. Kennewell, R. Westwood, J. Chem. Soc. Perkin Trans. 1: 687 (1984)), benzyl alcohol (1.23 mL, 11.9 mmol), triphenylphosphine (4.25 g, 16.2 mmol) under a N2 atmosphere in THF (100.0 mL) was treated with diethyl azodicarboxylate (2.55 mL, 16.2 mmol). The mixture was allowed to stir for 4 h then quenched with H2O. The mixture was then extracted with hexane (3×50 mL), the organic layers combined, dried with Na2SO4, and the solvent removed in vacuo. The residue was then submitted to column chromatography (SiO2 260-400 mesh, 4:1 hexanes: ethyl acetate) to provide the title compound (1.852 g, m.p. 99°-101° C.) as a solid. 'H NMR (400 MHz, CDCl3) δ 7.445-7.305 (m, 6H), 7.272-7.247 (m, 2H), 5.084 (s, 2H), 3.079 (m, 2H), 2.723-2.694 (m, 2H) .

Workup

  1. customthen quenched with H2O
  2. extractionThe mixture was then extracted with hexane (3×50 mL)
  3. dry with materialdried with Na2SO4
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-46a45879135d4d3a8ea3d8c193d90956
Source dataset
uspto-grants-1996_04
Patent number
US05504104

Reaction notes

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