Triethylamine → Diethyl(E)-2-{-4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate

HRID 229175

反応式

HRID 229175 の反応式
OC1C=CC(C(=C2CCOCC2)C2C=CC(/C=C/C(OC(C)(C)C)=O)=CC=2)=CC=1.Br[C:31]1[CH:36]=[CH:35][C:34]([C:37](=[C:45]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]2)[C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=2)=[CH:33][CH:32]=1.[CH:52]([P:54](=[O:61])([O:58][CH2:59][CH3:60])[O:55][CH2:56][CH3:57])=[CH2:53].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>[C:45]1(=[C:37]([C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=2)[C:34]2[CH:33]=[CH:32][C:31](/[CH:53]=[CH:52]/[P:54](=[O:61])([O:58][CH2:59][CH3:60])[O:55][CH2:56][CH3:57])=[CH:36][CH:35]=2)[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 69629Diethyl vinylphosphonateHCID 80271Tri-o-tolylphosphineHCID 686541254-[(4-Bromophenyl)(cycloheptylidene)methyl]phenolHCID 86613505tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoate

生成物 1

HCID 86613508Diethyl(E)-2-{-4-[cycloheptylidene(4-hydroxyphenyl)methyl]phenyl}ethenylphosphonate収率 28%

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)cycloheptylidene)methyl]phenol (9) (0.146 g, 0.409 mmole), diethyl vinylphosphonate (0.190 mL, 1.24 mmole), P(o-tolyl)3 (0.0123 g, 0.0404 mmole), Et3N (0.170 mL, 1.22 mmole), Pd(OAc)2 (0.0046 g, 0.0205 mmole) and DMF (1.5 mL) yielded 63 (0.0502 g, 28%) as a white solid. 1H NMR (DMSO-d6): δ 9.28 (s, 1H), 7.57 (d, J=8.3 Hz, 2H), 7.30 (dd, J=22.7, 17.6 Hz, 1H), 7.11 (d, J=8.3 Hz, 2H), 6.89 (d, J=8.4 Hz, 2H), 6.65 (d, J=8.4 Hz, 2H), 6.48 (dd, J=22.7, 17.6 Hz, 1H), 4.01-3.91 (m, 4H), 2.20 (m, 4H), 1.50 (m, 8H), 1.21 (m, 6H).

出典と根拠

ORDレコード
ord-1b1b15e18c6645a29627d07f30a23824
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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