Dimethylformamide → HCID 59314121, compound

HRID 1047831Notes

Reaction equation

HRID 1047831 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(C(=O)C2C=CC=C(C)C=2O)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[C:25]([O-:28])([O-])=O.[K+].[K+].Br[CH2:32][C:33]#[C:34][CH3:35].C[N:37]([CH:39]=[O:40])C>>[CH2:1]([O:3][C:4]([C:6]1([NH:37][C:39](=[O:40])[C:32]2[CH:7]=[CH:6][CH:4]=[C:34]([CH3:35])[C:33]=2[O:28][CH2:25][C:9]#[C:8][CH3:13])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 68590699HCID 68590699, compound

Product 1

HCID 59314121HCID 59314121, compound

Procedure

A 100 mL round bottom flask containing the 2-(hydroxy-3-methyl-benzoyl)-indan-2-carboxylic acid ethyl ester (0.62 g, 1.87 mmol) is charged with DMF (3 mL) and a stirring bar is added. After dissolution of the starting material, the K2SO4 (0.791 g, 5.95 mmol) is added followed by a solution of 1-bromo-2-butyne (537 μL, 5.95 mmol). After stirring for 110 h tlc analysis (silica, 1:1 EtOAc/heptanes) indicates that the starting material is consumed. The material is cleanly converted to a UV positive spot with a slightly lower Rf. The reaction is diluted with EtOAc (80 mL) and filtered through a pad of Celite. The filtrate is transferred to a separatory funnel. This is washed repeatedly with a saturated aqueous solution of NaHCO3 (2×50 mL) and brine (50 mL), dried over MgSO4, filtered and evaporated in vacuo to yield 0.75 g of a light brown oil. This is purified (silica, 40 g ISCO column 10% EtOAc in heptanes for 3 column volumes followed by a linear gradient to 50% EtOAc in heptanes for 10 column volumes). 17 mL fractions of UV positive eluent are collected. Fractions 2 through 8 are combined, evaporated in vacuo and pumped dry to yield 0.79 g of a white solid.

Workup

  1. additionis added
  2. dissolutionAfter dissolution of the starting material
  3. customis consumed
  4. additionThe reaction is diluted with EtOAc (80 mL)
  5. filtrationfiltered through a pad of Celite
  6. customThe filtrate is transferred to a separatory funnel
  7. washThis is washed repeatedly with a saturated aqueous solution of NaHCO3 (2×50 mL) and brine (50 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-03341fd6b5584202b1f759b960ce215a
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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