Water → HCID 23003909, compound

HRID 396720Notes

Reaction equation

HRID 396720 reaction equation
[Na].[C:2]([O:9][CH3:10])(=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[C:11]([N:18]1[C:26]2[C:21](=[CH:22][C:23]([CH:27]=[CH:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:25]=2)[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].O>CO.O1CCCC1>[C:11]([N:18]1[C:26]2[C:21](=[CH:22][C:23]([CH:27]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:3]([C:2]([O:9][CH3:10])=[O:8])[C:4]([O:6][CH3:7])=[O:5])=[CH:24][CH:25]=2)[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 7943Dimethyl malonateHCID 5360545SodiumHCID 54483034HCID 54483034, compound

Product 1

HCID 23003909HCID 23003909, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of sodium (156 mg) in methanol (15 ml) was treated with dimethyl malonate (0.8 ml) and after stirring for 15 minutes the mixture was then treated with a solution of methyl 3-(1-boc-2,3-dihydro-1H-indol-5-yl)acrylate [1.0 g, reference Example 7(b)] in tetrahydrofuran (15 ml). The mixture was stirred at reflux for 3 hours, then cooled to room temperature, then treated with water (2 ml) and then evaporated. The residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with fresh ethyl acetate. The combined organic layer and extracts were washed with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (15:85, v/v) to give the title compound (530 mg) as a clear oil. MS (ES+) 458 (MNa+). MS (ES−) 434 (M−).

Workup

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 3 hours
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with fresh ethyl acetate
  7. washThe combined organic layer and extracts were washed with brine
  8. customdried
  9. customevaporated
  10. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (15:85

Sources & evidence

ORD record
ord-bac7a9515a5e4cb28fd56aa6983f0a98
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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