Ethyl formate → Ethyl 2-[(2H-1,3-benzodioxol-5-yl)methyl]-3-oxopropanoate

HRID 1445306Notes

Reaction equation

HRID 1445306 reaction equation
[H-].[Na+].[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][C:5]=2[O:4]1.[CH:19](OCC)=[O:20]>O1CCCC1>[CH:19]([CH:13]([CH2:12][C:7]1[CH:8]=[CH:9][C:10]2[O:11][CH2:3][O:4][C:5]=2[CH:6]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:20]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 81545Ethyl 1,3-benzodioxole-5-propionate

Product 1

HCID 10060648Ethyl 2-[(2H-1,3-benzodioxol-5-yl)methyl]-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

First, 42.4 g of 60% NaH was suspended in 500 ml of tetrahydrofuran (THF). 84.5 g (purity: 93.7% by weight) of ethyl 3-(3,4-methylenedioxyphenyl)-propionate was dissolved in 100 ml of THF and added dropwise to the suspension solution prepared above at room temperature. After the resultant suspension solution was raised in temperature to 40° C. and stirred for 15 minutes, 131 g of ethyl formate was added dropwise for 2.5 hours to the suspension solution and stirred for a further 3 hours.

Workup

  1. additionadded dropwise to the suspension solution
  2. customprepared above at room temperature
  3. stirringstirred for a further 3 hours

Sources & evidence

ORD record
ord-98f38d7cc9aa4ea591aa80a17b083bf6
Source dataset
uspto-grants-2010_02
Patent number
US07666659B2

Reaction notes

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