3-Phenyl-1,5-dioxaspiro[3.2]hexane → 2-Hydroxymethyl-3-phenyl-2-(tetrazol-2-yl)oxetane

HRID 898686Notes

Reaction equation

HRID 898686 reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.[C:6]1([CH:12]2[C:15]3([CH2:17][O:16]3)[O:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[OH:16][CH2:17][C:15]1([N:2]2[N:3]=[N:4][CH:5]=[N:1]2)[CH:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:13][O:14]1

Participants

4

Reactant 2

HCID 105831113-Phenyl-1,5-dioxaspiro[3.2]hexaneHCID 178418441HCID 178418441, compound

Product 1

HCID 685269962-Hydroxymethyl-3-phenyl-2-(tetrazol-2-yl)oxetaneYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1H-Tetrazole (0.078 g, 1.1 mmol) in dry THF (2 mL) was added dropwise to a stirred solution under N2 of 3-phenyl-1,5-dioxaspiro[3.2]hexane (0.15 g, 0.94 mmol) in dry THF (2 mL) at 0° C. The reaction mixture was stirred for 1 hour and then concentrated. The resultant yellow oil was purified by flash chromatography on silica gel (CH2Cl2/methanol 100:0 to 98:2) to provide 2-hydroxymethyl-3-phenyl-2-(tetrazol-2-yl)oxetane as a pale yellow oil (0.090 g, 42%): IR (CDCl3) 3436 (br), 2916, 1319, 1054, 953 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.70 (s, 1H), 7.42 (m, 5H), 5.37 (dd, J=8.6, 6.9 Hz, 1H), 5.16 (dd, J=8.6, 6.1 Hz, 1H), 5.08 (dd, J=6.2, 6.2 Hz, 1H), 4.21 (dd, J=13.5, 7.5 Hz, 1H), 4.17 (dd, J=13.5, 7.4 Hz, 1H), 1.86 (dd, J=7.4, 7.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 153.1, 133.2, 129.1, 128.5, 128.1, 100.9, 69.6, 62.6, 47.8; MS (EI) m/z 204 (M+—N2), 185, 173, 104 (100), 91, 78; Anal. calculated for C11H12N4O2: C, 56.89; H, 5.21; N, 24.12. Found: C, 56.76; H, 5.14; N, 23.78.

Workup

  1. concentrationconcentrated
  2. customThe resultant yellow oil was purified by flash chromatography on silica gel (CH2Cl2/methanol 100:0 to 98:2)

Sources & evidence

ORD record
ord-f94502e2981e4db9bb64b62891d30919
Source dataset
uspto-grants-2008_04
Patent number
US07351827B2

Reaction notes

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