Benzyl Bromide → HCID 67685633, compound

HRID 1078503Notes

Reaction equation

HRID 1078503 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13](/[C:19](/[CH3:30])=[CH:20]\[C:21]4[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1.[Hg]>[C:1]12([C:11]3[CH:12]=[C:13](/[C:19](/[CH3:30])=[CH:20]/[C:21]4[CH:29]=[CH:28][C:24]([C:25]([O:27][CH2:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[O:26])=[CH:23][CH:22]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 19429709HCID 19429709, compound

Product 1

HCID 67685633HCID 67685633, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2 g (5 mmol) of 4-[(Z)-2-(3-(1-adamantyl)-4-methoxyphenyl)propenyl]benzoic acid obtained in Example 23(c) in 900 ml of THF are irradiated under UV by means of a HANOVIA mercury lamp (550 W) for 10 h at room temperature, to give a 1/1 mixture of E and Z isomers. After evaporation of the THF, this mixture is treated with 190 mg (6 mmol) of 80% NaH in oil and 0.83 ml (7 mmol) of benzyl bromide. After the same treatment as in Example 1(a), followed by a recrystallization from hexane, 0.54 g of benzyl 4-[(E)-2-(3-(1-adamantyl)-4-methoxyphenyl)propenyl]benzoate is isolated which melts at 230°-240° C.

Workup

  1. customto give
  2. additiona 1/1 mixture of E and Z isomers
  3. customAfter evaporation of the THF
  4. customAfter the same treatment as in Example 1(a), followed by a recrystallization from hexane

Sources & evidence

ORD record
ord-aee508a7af4641f399ab6e05d31cd92d
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

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