Hydrochloric Acid → HCID 14515317, compound

HRID 1646614Notes

Reaction equation

HRID 1646614 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].I[C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][CH:16]2[O:21][Si](C)(C)C.Cl>CN1CCN(C)C1=O>[C:3]([CH:5]([C:12]1[C:13]2[CH2:14][CH2:15][CH:16]([OH:21])[C:17]=2[CH:18]=[CH:19][CH:20]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 19801180HCID 19801180, compound

Product 1

HCID 14515317HCID 14515317, compound

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent3×

Procedure

6 ml of 1,3-dimethyl-2-imidazolidone and 0.99 g of sodium hydride at 50% are cooled to +15° C., 2.2 ml of ethyl cyanacetate in 10 ml of 1,3-dimethyl-2-imidazolidone is added over 5 minutes, with agitation for 40 minutes. 4.39 g of cuprous iodide, 3.62 g of 4-iodo-1-trimethylsilyloxy indane and 4 ml of 1,3-dimethyl-2-imidazolidone are added. The mixture is taken to 100° C. for 4 hours. After cooling, it is poured into 100 ml of 2N hydrochloric acid, filtered on celite, and rinsed with water; the filtrate is extracted with isopropyl ether, washed with a saturated solution of sodium bicarbonate and with water, dried and brought to dryness. The residue is chromatographed on silica in a hexane-ethyl acetate mixture (1-1) and 1.22 g of expected product is obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered on celite
  3. washrinsed with water
  4. extractionthe filtrate is extracted with isopropyl ether
  5. washwashed with a saturated solution of sodium bicarbonate and with water
  6. customdried
  7. customThe residue is chromatographed on silica in a hexane-ethyl acetate mixture (1-1)

Sources & evidence

ORD record
ord-9d7fa53ff335449a9cb5887e54ced146
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

Loading…