Dimethyldioxirane → 3-Phenyl-1,5-dioxaspiro[3.2]hexane

HRID 898683Notes

Reaction equation

HRID 898683 reaction equation
[CH2:1]=[C:2]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:4][O:3]1.CC1(C)O[O:14]1>C(Cl)Cl>[C:6]1([CH:5]2[C:2]3([CH2:1][O:14]3)[O:3][CH2:4]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 115197DimethyldioxiraneHCID 108445172-Methylene-3-phenyloxetane

Product 1

HCID 105831113-Phenyl-1,5-dioxaspiro[3.2]hexaneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methylene-3-phenyloxetane (0.10 g, 0.69 mmol) in dry CH2Cl2 (˜0.5 M) was cooled to −78° C. A solution of DMDO (˜0.35 M in CH2Cl2, 1.0-1.2 equiv) was added dropwise with stirring. The reaction mixture was stirred at −78° C. for 1 hour after which the solvent was removed in vacuo to give 3-phenyl-1,5-dioxaspiro[3.2]hexane as a colorless oil (0.11 g, 99%) and as a mixture of diastereomers (93:7). Major diastereomer: 1H NMR (400 MHz, CDCl3) δ 7.33 (m, 5H), 4.85 (m, 1H), 4.49 (m, 2H), 2.93 (d, J=3.4 Hz, 1H), 2.54 (d, J=3.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 136.6, 128.9, 127.8, 127.5, 95.0, 70.1, 50.5, 47.9. Minor diastereomer: 1H NMR (400 MHz, CDCl3) δ 7.33 (m, 5H), 4.85 (m, 1H), 4.65 (app t, J=6.6 Hz, 1H), 4.58 (dd, J=6.3, 5.0 Hz, 1H), 3.06 (d, J=3.4 Hz, 1H), 2.76 (d, J=3.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 135.5, 129.3, 128.6, 128.2, 92.7, 72.0, 51.4, 46.7; HRMS (FAB) calculated for C10H11O2 (M++1) m/z: 163.0759. Found: 163.0762.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 1 hour after which the solvent
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-967836be35fc45e7be1bb85c03ecd128
Source dataset
uspto-grants-2008_04
Patent number
US07351827B2

Reaction notes

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