Triethylamine → Ethyl(2E)-3-{4-[(4-hydroxyphenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoate

HRID 229167Notes

Reaction equation

HRID 229167 reaction equation
OC1C=CC(C(=C2CCOCC2)C2C=CC(/[CH:15]=[CH:16]/[C:17]([O:19][C:20](C)(C)[CH3:21])=[O:18])=CC=2)=CC=1.Br[C:31]1[CH:36]=[CH:35][C:34]([C:37](=[C:45]2[CH2:50][C:49]([CH3:52])([CH3:51])[O:48][C:47]([CH3:54])([CH3:53])[CH2:46]2)[C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=2)=[CH:33][CH:32]=1.C(OCC)(=O)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:44][C:41]1[CH:42]=[CH:43][C:38]([C:37](=[C:45]2[CH2:46][C:47]([CH3:53])([CH3:54])[O:48][C:49]([CH3:51])([CH3:52])[CH2:50]2)[C:34]2[CH:33]=[CH:32][C:31](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:36][CH:35]=2)=[CH:39][CH:40]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 686543254-[(4-Bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenolHCID 86613505tert-Butyl (2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoate

Product 1

HCID 68978687Ethyl(2E)-3-{4-[(4-hydroxyphenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenyl}prop-2-enoateYield 69%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Following the procedure described for compound 47, 4-[(4-bromophenyl)(2,2,6,6-tetramethyltetrahydro-4H-pyran-4-ylidene)methyl]phenol (3) (0.152 g, 0.379 mmole), ethyl acrylate (0.125 mL, 1.15 mmole), P(o-tolyl)3 (0.0126 g, 0.041 mmole), Et3N (0.160 mL, 1.15 mmole), Pd(OAc)2 (0.0044 g, 0.020 mmole) and DMF (1.5 mL) afforded 0.110 g (69%) of compound 54 as a white solid. 1H NMR (CDCl3): δ 7.65 (d, J=16.0 Hz, 1H), 7.45 (d, J=8.1 Hz, 2H), 7.18 (d, J=8.1 Hz, 2H), 7.03 (d, J=8.4 Hz, 2H), 6.77 (d, J=8.4 Hz, 2H), 6.40 (d, J=16.0 Hz, 1H), 4.84 (s, 1H), 4.25 (q, J=7.1 Hz, 2H), 2.25 (s, 2H), 2.24 (s, 2H), 1.34 (t, J=7.1 Hz, 3H), 1.23 (s, 6H), 1.22 (s, 6H).

Sources & evidence

ORD record
ord-9554f7f39c8f400583b2cb56b6903573
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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