Allyl bromide → HCID 18665761, compound

HRID 399251Notes

Reaction equation

HRID 399251 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[C@H:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[C@H:10]2[C:31]([OH:33])=[O:32])=[C:5]([O:34][CH2:35][O:36][CH3:37])[CH:4]=1.[CH2:38]1[CH2:48]CN2C(=NCCC2)C[CH2:39]1.C(Br)C=C>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[C@H:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[C@H:10]2[C:31]([O:33][CH2:48][CH:38]=[CH2:39])=[O:32])=[C:5]([O:34][CH2:35][O:36][CH3:37])[CH:4]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54356477HCID 54356477, compound

Product 1

HCID 18665761HCID 18665761, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(1S,2R,3S)-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid (4.8 g, 9.5 mmol) was dissolved in dry acetonitrile (30 ml) and DBU (1.7 ml, 11.4 mmol) was added followed by allyl bromide (3.4 g, 28. mmol). After stirring for 0.5 h. the product was partitioned between 3M aqueous HCl and ethyl acetate. The organic layer was washed with water and brine, then dried (MgSO4 anhyd.) filtered and evaporated to give an oil. The product was purified by column chromatography to provide the title compound as a pale yellow oil (5.7 g, quantitative).

Workup

  1. customwas partitioned between 3M aqueous HCl and ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4 anhyd.)
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil
  7. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-53db6a4dcaf248d0ad52850392bf8486
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

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