Boron trifluoride → HCID 57633598, compound

HRID 2108938Notes

Reaction equation

HRID 2108938 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[C:5]([CH3:10])=[CH:4][C:3]=1[OH:11].B(F)(F)F.[CH3:16][C:17]1[S:18][C:19]([CH3:27])=[CH:20][C:21]=1[C:22](O)([CH:24]=[CH2:25])[CH3:23].C(O)=C>O1CCOCC1>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[C:5]([CH3:10])=[C:4]2[C:3]=1[O:11][C:22]([C:21]1[CH:20]=[C:19]([CH3:27])[S:18][C:17]=1[CH3:16])([CH3:23])[CH2:24][CH2:25]2

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 18461306HCID 18461306, compoundHCID 66978118HCID 66978118, compound

Product 1

HCID 57633598HCID 57633598, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
120 °C

Procedure

To a solution of 2-chloro-3,5-dimethyl-benzene-1,4-diol (520 mg) and BF3 etherate (1.28 g) in dioxane (10 mL) at 120° C. was added slowly a solution of the vinyl alcohol 2-(2,5-dimethyl-thiophen-3-yl)-but-3-en-2-ol (600 mg) in 2 mL of dioxane in 30 min. After completion, the solution was stirred at 120° C. for 3 h. Workup and purification by silica gel column chromatography eluting with 10% EtOAc in hexane gave 50 mg off-white solid 4-Chloro-6-(2,5-dimethyl-thiophen-3-yl)-1,3,6-trimethyl-5,6,7,8-tetrahydro-naphthalen-2-ol. 1H NMR (300 MHz, CDCl3) 8:6.52 (s, 1H), 4.29 (s, 1H, OH), 2.63-2.33 (3s+m, 12H), 2.06-2.01 (s+m, 4H), 1.62 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3 δ:145.40, 143.98, 139.90, 134.97, 132.28, 125.68, 121.24, 120.34, 119.97, 119.57, 78.05, 32.85, 28.52, 21.74, 15.49, 14.96, 13.49, 11.77 ppm. MS m/z: 337 (M+H+).

Workup

  1. customWorkup and purification by silica gel column chromatography
  2. washeluting with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-86962947a83748898165b39bec2d39a6
Source dataset
uspto-grants-2009_04
Patent number
US07514461B2

Reaction notes

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