3-Phenyl-1,5-dioxaspiro[3.2]hexane → 2-(Benzotriazol-2-yl)-2-(hydroxymethyl)-3-phenyloxetane

HRID 898684Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[C:10]1([CH:16]2[C:19]3([CH2:21][O:20]3)[O:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[N:1]1[N:2]([C:19]2([CH2:21][OH:20])[CH:16]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:17][O:18]2)[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 0 °C

Procedure

Benzotriazole (0.15 g, 1.3 mmol) in dry CH2Cl2 (4 mL) at 0° C. was added to a stirred solution under N2 of 3-phenyl-1,5-dioxaspiro[3.2]hexane (0.21 g, 1.3 mmol) in dry CH2Cl2 (4 mL) at 0° C. The reaction mixture was left to stir for 3 hours at 0° C. It was then concentrated to provide a light brown oil. The residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc 80:20) to give 2-(benzotriazol-2-yl)-2-(hydroxymethyl)-3-phenyloxetane as a white solid (0.15 g, 41%): mp 119-123° C.; IR (film) 3437 (br), 3094, 3064, 2941, 1560, 1499 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.95 (d, J=8.1 Hz, 2H), 7.35 (m, 7H), 5.42 (dd, J=8.7, 7.0 Hz, 1H), 5.20 (dd, J=8.7, 6.0 Hz, 1H), 5.09 (dd, J=6.8, 6.0 Hz, 1H), 4.25 (dd, J=13.0, 7.7 Hz, 1H), 4.20 (dd, J=13.0, 7.0 Hz, 1H), 2.6 (dd, J=7.3, 7.3 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 144.8, 134.3, 129.3, 128.6, 128.5, 127.8, 119.1, 102.2, 69.8, 63.8, 48.8; MS (EI) m/z 281 (M+), 251, 162, 104 (100), 91; HRMS (FAB) calculated for C16H16N3O2 (M++H) m/z 282.1242. Found: 282.1248; Anal. calculated for C16H15N3O2: C, 68.31; H, 5.37; N, 14.94. Found: C, 68.13; H, 5.40; N, 14.97.

Workup

waitThe reaction mixture was left
concentrationIt was then concentrated
customto provide a light brown oil
customThe residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc 80:20)

Sources & evidence

ORD record: ord-37573fb9ab3b4e2797e0ba6fa440d158
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351827B2

Reaction notes

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