Dimethyldioxirane → 2-Benzyloxymethyl-1,5-dioxaspiro[3.2]hexane

HRID 898688Notes

Reaction equation

HRID 898688 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[O:13][C:12](=[CH2:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)O[O:17]1>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:11][C:12]2([CH2:14][O:17]2)[O:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 115197DimethyldioxiraneHCID 596930374-Benzyloxymethyl-2-methyleneoxetane

Product 1

HCID 596930362-Benzyloxymethyl-1,5-dioxaspiro[3.2]hexane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-benzyloxymethyl-2-methyleneoxetane (0.19 g, 0.98 mmol) in dry CH2Cl2 (2 mL), was cooled to −78° C. Dimethyldioxirane (0.5M in CH2Cl2, 2 eq) was added dropwise to the stirred solution. The reaction mixture was stirred for 1 hour more, then quickly warmed to room temperature, and, subsequently, the solvent was removed in vacuo. 2-Benzyloxymethyl-1,5-dioxaspiro[3.2]hexane was isolated as pale yellow oil (0.19 g, 95%) and as a mixture of diastereoisomers (72:28). Major diastereomer: 1H NMR (400 MHz, CDCl3) δ 7.30 (m, 5H), 4.83 (m, 1H), 4.67 (d, J=12.2 Hz, 1H), 4.62 (d, J=12.2 Hz, 3H), 3.71 (m, 2H), 3.06 (dd, J=12.6, 2.7 Hz, 1H), 3.04 (dd, J=12.6, 4.2 Hz, 1H), 2.93 (d, J=3.3 Hz, 1H), 2.71 (d, J=3.3 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 138.2, 128.6, 127.9, 127.8, 89.0, 73.8, 73.5, 72.1, 51.4, 31.4. Minor diastereomer: 1H NMR (400 MHz, CDCl3) δ 7.30 (m, 5H), 4.70 (m, 1H), 3.71 (m, 2H), 3.19 (dd, J=12.6, 7.2 Hz, 1H), 2.94 (d, J=3.6 Hz, 1H), 2.88 (dd, J=12.7, 5.6 Hz, 1H), 2.75 (d, J=3.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 138.2, 128.6, 127.9, 127.8, 88.2, 73.9, 72.6, 72.5, 51.3, 31.6.

Workup

  1. customsubsequently, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-4622db31779a4e0386c85ba7706e94f7
Source dataset
uspto-grants-2008_04
Patent number
US07351827B2

Reaction notes

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