2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 19767522, compound

HRID 1590609Notes

Reaction equation

HRID 1590609 reaction equation
[CH3:1][C:2]1([CH3:27])[O:7][CH2:6][C:5]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)([CH2:8][O:9]CC2C=CC(OC)=CC=2)[CH2:4][O:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl.O>[CH3:1][C:2]1([CH3:27])[O:3][CH2:4][C:5]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)([CH2:8][OH:9])[CH2:6][O:7]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 19767493HCID 19767493, compound

Product 1

HCID 19767522HCID 19767522, compound

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

To a stirred solution of 2,2-dimethyl-5-(3,4-difluorophenyl)-5-(4-methoxybenzyloxymethyl)-1,3-dioxane (360 mg, 1 mmol) in 10 ml of an 18:1 v/v mixture of dichloromethane-water was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (350 mg, 1.5 mmol) in small portions. The reaction mixture was stirred for 4 hours, then filtered and evaporated; purification on a silica column eluting with dichloromethane/methanol (19:1 v/v) afforded 2,2-dimethyl-5-(3,4-difluorophenyl) 5-hydroxymethyl-1,3-dioxane as a yellow oil. Nmr δ 7.2-7.0 (3H,m), 4.05 (2H,d), 4.00 (2H,d), 4.00 (2H,s), 1.75 (1H,broad), 1.4 (6H,d).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. custompurification on a silica column
  4. washeluting with dichloromethane/methanol (19:1 v/v)

Sources & evidence

ORD record
ord-6e718f08c9934b038dd997d823ea4ca7
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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