Formaldehyde → HCID 66597447, compound

HRID 1627798Notes

Reaction equation

HRID 1627798 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:3]=1[CH2:21][C:22]([O:24][CH3:25])=[O:23].[Li+].[CH3:27][Si]([N-][Si](C)(C)C)(C)C.C1COCC1.C=O>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:3]=1[C:21](=[CH2:27])[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 66597278HCID 66597278, compound

Product 1

HCID 66597447HCID 66597447, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure C from methyl [2-methyl-4-p-tolyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3yl]acetate (0.386 g; 1.1 mmol), LHMDS 1N in THF (1.21 mL; 1.21 mmol), para-formaldehyde (0.050 g; 1.65 mmol) in DMF (4 mL) for 4 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (3-100%) in heptane furnished 0.154 g (36%) of the title compound as a light yellow solid.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (3-100%) in heptane

Sources & evidence

ORD record
ord-41308ee30a444744acae6e32a4455893
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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