2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13075704, compound

HRID 2198538Notes

Reaction equation

HRID 2198538 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]([OH:33])([CH2:8][CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@:31]2([CH3:32])[C@H:16]([C@H:17]3[C@H:28]([CH2:29][CH2:30]2)[C@:26]2([CH3:27])[C:20]([CH2:21][C@H:22]([CH2:24][CH2:25]2)[OH:23])=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)[CH3:12])[C:4]([F:7])([F:6])[F:5].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[F:1][C:2]([F:34])([F:35])[C:3]([OH:33])([CH2:8][CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@:31]2([CH3:32])[C@H:16]([C@H:17]3[C@H:28]([CH2:29][CH2:30]2)[C@:26]2([CH3:27])[C:20](=[CH:21][C:22](=[O:23])[CH:24]=[CH:25]2)[CH:19]=[CH:18]3)[CH2:15][CH2:14]1)[CH3:12])[C:4]([F:5])([F:7])[F:6]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 54047708HCID 54047708, compound

Product 1

HCID 13075704HCID 13075704, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (2) (893 mg) and DDQ (2.2 g) in dioxane (50 ml) was stirred for 15 hr at 80°-90° C. and then refluxed for 4 hr. After cooling to room temperature the precipitate was filtered off and the filtrate was diluted with ether which was successively washed with 1 N-KOH and brine. The extract was purified by silica gel column (AcOEt-n-hexane, 1:20 to give 490 mg (55%) of the trienone (3); mp 166°-168° C. (from AcOEt-cyclohexane), MS m/e 504(M+), 489; IR(KBr), 3180, 1650, 1595 cm-1 ; NMR(CDCl3)δ0.72(s, 18-H3), 0.95(d, J=6 Hz, 21-H3), 1.18 (s, 19-H3), 5.88-6.33(4H, m, 2-,4-,6- and 7-H), 7.04(1H, d, J=10 Hz, 1-H). Anal. Calcd., For C27H34F6O2 ; C, 64.27; H, 6.79; F, 22.59. Found, C, 64.17; H, 6.81; F, 22.34.

Workup

  1. temperaturerefluxed for 4 hr
  2. filtrationwas filtered off
  3. additionthe filtrate was diluted with ether which
  4. washwas successively washed with 1 N-KOH and brine
  5. customThe extract was purified by silica gel column (AcOEt-n-hexane, 1:20

Sources & evidence

ORD record
ord-9b234ba093d24c5f9cd7314a0e10894d
Source dataset
uspto-grants-1982_11
Patent number
US04358406

Reaction notes

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