Hydrochloric Acid → HCID 178445647, compound

HRID 1674447Notes

Reaction equation

HRID 1674447 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[CH2:7][CH2:6]1)[CH2:2][CH:3]=[CH2:4].C([Li])(CC)C.B(OC)(OC)[O:27]C.OO.Cl>C1COCC1.C1(C)C=CC=CC=1.CCCCCC.C1CCCCC1>[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([OH:27])=[C:15]([F:19])[C:14]=2[F:20])[CH2:7][CH2:6]1)[CH2:2][CH:3]=[CH2:4]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 178418400CID 53628100HCID 178445646HCID 178445646, compound

Product 1

HCID 178445647HCID 178445647, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8078CyclohexaneSolvent

Procedure

3 g of 1-((trans-4-(3-butenyl)cyclohexyl)methoxy)-2,3-difluorobenzene was dissolved in 30 mL of THF, and 11.7 mL of sec-butyllithium (1.01 M cyclohexane, a hexane solution) was added dropwise thereto at an internal temperature of −40 to −60° C. Then, the solution was stirred for 30 min. To this solution, 1.3 g of trimethyl borate was added, and the solution was heated to room temperature. Then, 1.8 mL of 30% hydrogen peroxide solution was added thereto, and the solution was stirred at 40° C. for 1 hours. To the solution, 5% hydrochloric acid was added, and the solution was stirred for 1 hour. Toluene was added thereto, and the organic layer was fractioned, washed with saturated saline, and then dried over anhydrous magnesium sulfate, to thereby obtain 4-((trans-4-(3-butenyl)cyclohexyl)methoxy)-2,3-difluorophenol.

Workup

  1. customat an internal temperature of −40 to −60° C
  2. stirringthe solution was stirred at 40° C. for 1 hours
  3. stirringthe solution was stirred for 1 hour
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-da31357484084469a67d517d1f88a9c7
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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