Methanol → HCID 66597506, compound

HRID 1627870Notes

Reaction equation

HRID 1627870 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[C:3]=1OC(=O)CCCC.[OH-:29].[Na+].[CH3:31][OH:32]>>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[C:3]=1[CH:1]([CH2:2][CH2:3][CH3:4])[C:31]([OH:32])=[O:29]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86762559HCID 86762559, compound

Product 1

HCID 66597506HCID 66597506, compoundYield 52%

Conditions

Temperature
60 °C

Procedure

To a solution of methyl [[2-methyl-4-(m-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoate (0.281 g; 0.65 mmol) in methanol (6.5 mL) was added a solution of sodium hydroxide 5 N (1.3 mL) and the mixture was heated at 60° C. for 18 h. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the mixture was acidified with HCl (1N) until pH 1. The organic layer was washed with brine, water, dried over magnesium sulphate and concentrated under reduced pressure. The crude residue was crystallized from a mixture ethyl acetate-heptane to furnish 0.129 g (52%) of the title compound as a light yellow solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with brine, water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was crystallized from a mixture ethyl acetate-heptane

Sources & evidence

ORD record
ord-db4746d0d1564eb1adefc2e459dfd509
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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