Sodium hydride → HCID 10577534, compound

HRID 1182015Notes

Reaction equation

HRID 1182015 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[C:11]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:12]=[C:13]([CH:17]=1)[C:14](O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(Cl)(=O)C([Cl:39])=O>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[C:11]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:12]=[C:13]([CH:17]=1)[C:14]([Cl:39])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 10719819HCID 10719819, compound

Product 1

HCID 10577534HCID 10577534, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 5-benzyloxy-3,4-di-t-butyldimethylsiloxybenzoic acid (1 g, 2 mmol) in 46 mL of benzene was added to a solution of NaH (80 mg, 2 mmol) in 2 mL of benzene. The resulting solution was stirred with oxalyl chloride (0.9 mL, 10 mmol) under Ar for 20 h. Removal of solvent afforded 0.93 g (91%) of 5-benzyloxy-3,4-di-t-butyldimethylsiloxybenzoyl chloride as a yellow solid.

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-6589ab332e03461d804abc32df12658d
Source dataset
uspto-grants-2007_10
Patent number
US07288273B1

Reaction notes

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