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

HRID 898685Notes

Reaction equation

HRID 898685 reaction equation
[NH:1]1[CH:5]=[CH: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>C(Cl)Cl>[OH:16][CH2:17][C:15]1([N:2]2[N:3]=[CH: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 178418936HCID 178418936, compound

Product 1

HCID 685273552-Hydroxymethyl-3-phenyl-2-(1,2,3-triazol-2-yl)oxetane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1H-1,2,3-triazole (0.043 g, 0.62 mmol) in dry CH2Cl2 (2 mL) was introduced to a stirred solution under N2 of 3-phenyl-1,5-dioxaspiro[3.2]hexane (0.10 g, 0.62 mmol) in dry CH2Cl2 (2 mL) at −78° C. After 3 hours at −78° C., the reaction was allowed to warm to room temperature; then, the solvent was evaporated in vacuo. The resultant oil was purified by flash chromatography on silica gel (CH2Cl2/EtOAc 95:5). 2-Hydroxymethyl-3-phenyl-2-(1,2,3-triazol-2-yl)oxetane was isolated as a pale yellow solid (0.076 g, 59%): mp 77.0-78.3° C.; IR (CDCl3) 3145, 3031, 2969, 1496, 1452, 1323, 1049 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.82 (s, 2H), 7.41 (m, 2H), 7.35 (m, 3H), 5.41 (dd, J=8.2, 7.7 Hz, 1H), 5.08 (dd, J=8.5, 6.0 Hz, 1H), 4.98 (dd, J=7.0, 6.0 Hz, 1H), 4.15 (dd, J=13.0, 7.6 Hz, 1H), 4.10 (dd, J=13.0, 7.6 Hz, 1H), 2.51 (t, J=7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 135.3, 134.1, 128.8, 128.1, 128.0, 99.7, 68.5, 62.9, 47.9; MS (EI) m/z 200 (M+—CH2O), 185, 104 (100), 78; Anal. calculated for C12H13N3O2: C, 62.33; H, 5.67; N, 18.17. Found: C, 62.58; H, 5.30; N, 17.94.

Workup

  1. customthen, the solvent was evaporated in vacuo
  2. customThe resultant oil was purified by flash chromatography on silica gel (CH2Cl2/EtOAc 95:5)

Sources & evidence

ORD record
ord-457737bbe15f4185ab2541087b795e9c
Source dataset
uspto-grants-2008_04
Patent number
US07351827B2

Reaction notes

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