Hydrochloric Acid → HCID 131725170, compound

HRID 498104Notes

Reaction equation

HRID 498104 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([CH:13]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18](=[O:23])[CH:17]([O:24][SiH:25]([CH3:27])[CH3:26])[CH2:16][CH2:15][CH2:14]1)([CH3:12])([CH3:11])[CH3:10].Cl>O1CCCC1.CCOCC>[C:1]1([C:18]2([OH:23])[CH2:19][CH2:20][CH2:21][CH2:22][CH:13]([C:9]([CH3:12])([CH3:10])[CH3:11])[CH2:14][CH2:15][CH2:16][CH:17]2[O:24][SiH:25]([CH3:27])[CH3:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 131725168HCID 131725168, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 131725170HCID 131725170, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

21 ml of a solution (1.0 M) of phenylmagnesium bromide in tetrahydrofuran was dissolved in 50 ml of anhydrous ether, and to the solution was added 1.5 g of the above product (b). The reaction solution was stirred at 40° C. for three and a half hours. The reaction solution was poured into ice water and adjusted to pH 4 by addition of 2N HCl, and extracted with ether. The organic layer was washed with a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated. The residue was subject to column chromatography on silica gel, and the eluate with ethyl acetate-hexane (1:20) was collected, to afford 1.1 g of the titled compound (c) as a colorless oily matter.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe eluate with ethyl acetate-hexane (1:20) was collected

Sources & evidence

ORD record
ord-bfe42ed9c5104d8e94aac9c2650cdb5d
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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