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Trimethyl orthoformate → (3-Benzyloxy-4-methoxy-benzylidene)-(2,2-dimethoxy-ethyl)-amine

HRID 1833132
Notes
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Reaction equation

HRID 1833132 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH:21]([O:24][CH3:25])[CH2:22][NH2:23].COC(OC)OC>ClCCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[N:23][CH2:22][CH:21]([O:24][CH3:25])[O:20][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 280250(3-Benzyloxy-4-methoxy-benzylidene)-(2,2-dimethoxy-ethyl)-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-Benzyloxy-4-methoxybenzaldehyde (2.42 g, 10 mmol), aminoacetaldehyde dimethylacetal (1.08 g, 10 mmol), and trimethylorthoformate (2.5 mL) were mixed in 1,2-dichloroethane (10 mL) at room temperature and stirred×2 hours. The solvent was removed in vacuo to give (3-benzyloxy-4-methoxy-benzylidene)-(2,2-dimethoxy-ethyl)-amine as a viscous oil, which was dissolved in diethyl ether (10 mL).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dd002ed3429243a4bc60aec239773f33
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07067529B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes