Hydrochloric Acid → HCID 60087333, compound

HRID 511987Notes

Reaction equation

HRID 511987 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]([CH3:18])([CH3:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:4][C:3]=1[O:19][CH3:20].[Li]CCCC.[B:26](OC)([O:29]C)[O:27]C.Cl>C1COCC1>[CH3:20][O:19][C:3]1[CH:4]=[C:5]([C:10]([CH3:18])([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:17])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[B:26]([OH:29])[OH:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 13843393HCID 13843393, compoundHCID 178418339Butyllithium

Product 1

HCID 60087333HCID 60087333, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 37.1 (2.78 g, 8.0 mmol) in anhydrous THF (20 ml) under an argon atmosphere at −78° C. was added n-BuLi (5.5 ml, 8.8 mmol using 1.6 M solution in hexane) over a 30 min period. Stirring was continued at −78° C. for 15 min and then trimethyl borate (2.7 ml, 24 mmol) was added. Following addition, the reaction mixture was allowed to warm to room temperature over 12 hours period. The pH was adjusted to 6.5 by addition of 5% aqueous HCl solution at 0° C., and the mixture was extracted with dichloromethane. The organic layer was washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (12% acetone in hexane) to give 38.1 as colorless oil, in 83% yield (2.1 g).

Workup

  1. additionaddition
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel (12% acetone in hexane)

Sources & evidence

ORD record
ord-746846050b37440daa1ce17928e08429
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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