Hydrogen Peroxide → HCID 178455768, compound

HRID 1674434Notes

Reaction equation

HRID 1674434 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C@H:17]2[CH2:22][CH2:21][C@H:20]([CH:23]=[CH2:24])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1.C([Li])(CC)C.B(OC)(OC)[O:31]C.OO>C1COCC1.C1(C)C=CC=CC=1.O.C1CCCCC1.CCCCCC>[F:8][C:7]1[C:2]([F:1])=[C:3]([O:9][CH2:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([C@H:17]3[CH2:22][CH2:21][C@H:20]([CH:23]=[CH2:24])[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)[CH:4]=[CH:5][C:6]=1[OH:31]

Participants

10

Reactant 4

HCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 178418400CID 53628100HCID 178455765HCID 178455765, compound

Product 1

HCID 178455768HCID 178455768, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
0 °C

Procedure

15.7 g of 2,3-difluoro-1-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxybenzene was dissolved in 80 mL of THF, and 51 mL of sec-butyllithium (1.01 M hexane, a cyclohexane solution) was added dropwise thereto at an internal temperature of −45° C. or lower. Then, further stirring was continued for 30 min. To this solution, 5.9 g of trimethyl borate was added dropwise at an internal temperature of −40° C. or lower, and further stirring was continued for 30 min, and then the temperature was increased to 0° C. Then, 16 mL of water was added dropwise, and then 16 mL of 15% hydrogen peroxide solution was further added dropwise for 30 min. The stirring was continued for 3 hours. Water and toluene were added thereto, and the organic layer was fractioned while the aqueous layer was extracted with toluene. The organic layers were combined, washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography and recrystallization, to thereby obtain 2,3-difluoro-4-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxyphenol.

Workup

  1. customat an internal temperature of −45° C.
  2. stirringlower, and further stirring
  3. waitwas continued for 30 min
  4. waitThe stirring was continued for 3 hours
  5. extractionwas extracted with toluene
  6. washwashed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by column chromatography and recrystallization

Sources & evidence

ORD record
ord-7292dab817764516b4ecf88316003a45
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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