Formaldehyde → 2-[2-[4-(3-Benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N+:25]([O-:27])=[O:26])=[C:18]([Cl:28])[CH:17]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]=[O:30].N12CCCN=C1CCCCC2.N12CCCC1=NCCC2.N12CCC(CC1)CN2.[OH-].[Na+].[OH-].[K+].[O:63]1[CH2:67]CCC1>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([N+:25]([O-:27])=[O:26])([CH2:67][OH:63])[CH2:29][OH:30])=[C:18]([Cl:28])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
10
Reactant 8
Product 1
Reagents, catalysts & solvents 1
Procedure
1-Benzyloxy-3-[3-chloro-4-(3-nitropropyl)phenylthio]benzene (8) is dissolved in an organic solvent, such as acetonitrile and tetrahydrofuran. While the mixture is chilled in an ice bath, a formaldehyde solution is added and the reaction is allowed to proceed at 0 to 60° C. for 1 to 3 hours in the presence of a base, such as 1,8-diazabicyclo[5.4.0]undeca-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, diazabicyclo[2.2.2]octane, trialkylamine, sodium hydroxide and potassium hydroxide. Subsequently, the product is treated to give 2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol (9) or a hydrate thereof.
Workup
- temperatureWhile the mixture is chilled in an ice bath
- additionSubsequently, the product is treated
Sources & evidence
- ORD record
- ord-9e11d5610dca4000a6cff8eb442b0183
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795472B2
Reaction notes
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