反应详情

4-Bromomethyl benzophenone (2) was prepared as described in Reference Example 1. 4-Bromomethyl benzophenone (2) was converted into 4-Hydroxylmethyl benzophenone (3) as described in Reference Example 2. To a solution of 3 (0.5 g, 3.4 mmol) in dry THF (10 ml) was added sodium hydride (0.3 g, 60% dispersion in mineral oil, 6.7 mmol). The mixture was stirred for 5 min, then allyl bromide (0.8 g, 6.7 mmol) was added. The mixture as stirred for 18 h. the quenched with water and concentrated in vacuo. The residue was portioned between DCM and water, the organic layer collected, dried over MgSO4 and concentrated. A mineral oil impurity was removed using a silica plug eluting with petrol then ethyl acetate to yield 9 (0.6 g, 92%) as a yellow oil; δH (CDCl3) 4.08 (dt, 2H, J=1.4, 5.5 Hz, OCH2CH═CH2), 4.60 (s, 2H, ArCH2O), 5.24 (ddt 1H, J=1.4, 3.2, 10.3 Hz, OCH2CH═CHH), 5.34 (ddt 1H, J=1.4, 3.2, 17.3 Hz, OCH2CH═CHH), 5.88-6.08 (m, 1H, OCH2CH═CHH), 7.42-7.50 (m, 4H, 3-, 3′-, 5-, 5′-H), 7.54-7.62 (m, 1H, 4′-H), 7.78-7.82 (m, 4H, 2-, 2′-, 6-, 6′-H) ppm; δC (CDCl3) 61.4, 71.3 (ArCH2O, OCH2CH═CH2), 117.3 (OCH2CH═CH2), 127.0, 128.1 (3-, 3′-, 5-, 5′-C), 129.8, 130.1 (2-, 2′-, 6-, 6′-C), 132.2 (4′-C), 134.3 (OCH2CH═CH2), 136.6, 137.5 (1-, 1′-C), 143.1 (4-C), 196.2 (C═O) ppm; νmax (thin film) 3061, 2855, 1658, 1609, 1447, 1412, 1278, 1089, 924 cm−1; m/z (Er) 252 ([M+], 85%), 222 (100%); found 252.1158, C17H16O2 requires 252.1150.

1. stirringThe mixture as stirred for 18 h. the
2. customquenched with water
3. concentrationconcentrated in vacuo
4. customthe organic layer collected
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customA mineral oil impurity was removed
8. washeluting with petrol