Diethyl Ether → HCID 18443102, compound

HRID 458885Notes

Reaction equation

HRID 458885 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([O:7][C:8](=[O:21])[C:9]([OH:20])([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:3]1.[Br:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOCC>C(Cl)(Cl)Cl.C(#N)C>[Br-:22].[OH:20][C:9]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[C:8]([O:7][CH:4]1[CH2:5][CH2:6][N+:2]([CH3:1])([CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:3]1)=[O:21]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 68522Benzene, (3-bromopropoxy)-HCID 69478495HCID 69478495, compound

Product 1

HCID 18443102HCID 18443102, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

0.66 g (0.002 mol) of 2-hydroxy-2,2-dithien-2-ylacetic acid 1-methylpyrrolidin-3-yl ester (Intermediate I-7) were dissolved in 9 ml of CHCl3 and 6 ml of acetonitrile. 1.6 ml of (3-bromopropoxy)benzene (2.15 g, 0.01 mol) were added and the mixture was stirred during 72 hours at room temperature under N2 atmosphere. Solvents were evaporated. Ether was added to the residue and the mixture stirred to obtain a solid. The solid was treated with ether several times, filtered and washed with ether. The yield was 0.75 g (69.4%) of the title compound as a mixture of four stereoisomers.

Workup

  1. customSolvents were evaporated
  2. additionEther was added to the residue
  3. stirringthe mixture stirred
  4. customto obtain a solid
  5. filtrationfiltered
  6. washwashed with ether
  7. additionThe yield was 0.75 g (69.4%) of the title compound as a mixture of four stereoisomers

Sources & evidence

ORD record
ord-db18bbe0905b440b929f6f957b6fa6a7
Source dataset
uspto-grants-2007_03
Patent number
US07192978B2

Reaction notes

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