Hydrochloric Acid → HCID 58151935, compound

HRID 1873316Notes

Reaction equation

HRID 1873316 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH:13]3[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]3)[CH2:9]2)=[CH:4][CH:3]=1.[Li]CCCC.B(OC)(OC)[O:28]C.OO.Cl>C1COCC1.O.C(O)(=O)C>[F:1][C:2]1[C:3]([OH:28])=[CH:4][C:5]2[CH2:6][CH2:7][CH:8]([CH:13]3[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14]3)[CH2:9][C:10]=2[C:11]=1[F:12]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 58151932HCID 58151932, compoundHCID 178418339Butyllithium

Product 1

HCID 58151935HCID 58151935, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

77.0 g (about 0.26 mol) of crude 7,8-difluoro-2-(4-propylcyclohexyl)-1,2,3,4-tetrahydronaphthalene are initially introduced in 500 ml of THF, and 200.0 ml (0.32 mol) of n-BuLi (15% soln. in hexane) are added at −70° C. After 3 h at this temperature, 37.0 ml (0.33 mol) of trimethyl borate are added dropwise, the batch is warmed to 0° C., and 80 ml of dilute acetic acid (about 30%) are added. The mixture is warmed to 30° C., and 70 ml of hydrogen peroxide solution (35%) are carefully added. When the addition is complete, the mixture is stirred at RT for 2 h. Water is added, and the batch is acidified using dil. hydrochloric acid. The solution is extracted a number of times with MTBE, and the combined organic phases are washed successively with water, sat. sodium chloride soln. and ammonium iron(II) sulfate soln. The solution is dried using sodium sulfate and evaporated to dryness. The crude product is purified by column chromatography (SiO2, toluene). The further purification is carried out by crystallisation from n-heptane, giving 3,4-difluoro-6-(4-propylcyclohexyl)-5,6,7,8-tetrahydronaphthalen-2-ol as a colourless solid.

Workup

  1. temperatureThe mixture is warmed to 30° C.
  2. additionWhen the addition
  3. extractionThe solution is extracted a number of times with MTBE
  4. washthe combined organic phases are washed successively with water, sat. sodium chloride soln
  5. customThe solution is dried
  6. customevaporated to dryness
  7. customThe crude product is purified by column chromatography (SiO2, toluene)
  8. customThe further purification
  9. customis carried out by crystallisation from n-heptane

Sources & evidence

ORD record
ord-49b678e38ecf43018f95f611461bedb6
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

Loading…