Sodium hydride → HCID 86761088, compound

HRID 644576Notes

Reaction equation

HRID 644576 reaction equation
[CH2:1](/[C:3](/[C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)=[CH:4]\[C:5]#[CH:6])[CH3:2].[H-].[Na+].[C:16]([O:24][CH2:25][C:26]1[CH:31]=[C:30]([CH2:32]Br)[CH:29]=[CH:28][C:27]=1[CH2:34][O:35][C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:16]([O:24][CH2:25][C:26]1[CH:31]=[C:30]([CH2:32][O:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7](/[C:3](/[CH2:1][CH3:2])=[CH:4]/[C:5]#[CH:6])[CH:8]=2)[CH:29]=[CH:28][C:27]=1[CH2:34][O:35][C:36](=[O:43])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 223456183,4-Bis(benzoyloxymethyl)benzyl bromideHCID 86761087HCID 86761087, compound

Product 1

HCID 86761088HCID 86761088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

610 mg (3.5 mmol) of 3-((E)-1-ethylbut-1-en-3-ynyl)phenol are dissolved in 80 ml of DMF. 150 mg (3.7 mmol) of sodium hydride are added, and the mixture is stirred at ambient temperature. 1.5 g (6.2 mmol) of 2-benzoyloxymethyl-5-bromomethylbenzyl benzoate are then added, and the medium is stirred for 2 hours. After the usual treatment and purification by chromatography on a silica gel column, a colorless oil is obtained (m=1.66 g; Y=88%).

Workup

  1. stirringthe medium is stirred for 2 hours
  2. customAfter the usual treatment and purification by chromatography on a silica gel column
  3. customa colorless oil is obtained (m=1.66 g; Y=88%)

Sources & evidence

ORD record
ord-31418f2cde194d139d2d7ddcf14a749c
Source dataset
uspto-grants-2010_04
Patent number
US07700657B2

Reaction notes

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