Triethylamine → tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}-2-methylprop-2-enoate

HRID 229172

反応式

HRID 229172 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Br[C:31]1C=CC(C(=C2CCOCC2)C2C=CC(O)=CC=2)=CC=1.C(OC(C)(C)C)(=O)C(C)=C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[C:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[CH3:31])/[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 11448tert-Butyl methacrylateHCID 80271Tri-o-tolylphosphineHCID 686541974-[(4-Bromophenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenolHCID 86613505tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoate

生成物 1

HCID 86613507tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}-2-methylprop-2-enoate収率 59%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

Following the procedure described for compound 47, from 4-[(4-bromophenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenol (46) (0.101 g, 0.293 mmole), tert-butyl methacrylate (0.095 mL, 0.585 mmole), P(o-tolyl)3 (0.0092 g, 0.0302 mmole), Et3N (0.125 mL, 0.897 mmole), Pd(OAc)2 (0.0038 g, 0.0169 mmole) and DMF (1.5 mL) yielded compound 59 (0.070 g, 59%) as a white solid. 1H NMR (CDCl3): δ 7.55 (s, 1H), 7.31 (d, J=8.1 Hz, 2H), 7.11 (d, J=8.1 Hz, 2H), 6.98 (d, J=8.5 Hz, 2H), 6.76 (d, J=8.5 Hz, 2H), 4.91 (s, 1H), 3.73 (m, 4H), 2.41 (m, 4H), 1.58 (s, 3H), 1.54 (s, 9H).

出典と根拠

ORDレコード
ord-d0a95525806e408d8c8cdd5f5aaa91a3
出典データセット
uspto-grants-2009_07
特許番号
US07560589B2

関連ノート

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