Water → HCID 13336381, compound

HRID 1788741Notes

Reaction equation

HRID 1788741 reaction equation
C([Li])CCC.[O:6]1[C:10]2([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)OCC1.[C:16]1([C:22]2[N:31]=[C:30]([C:32](OCC)=[O:33])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CCCCCC.O1CCCC1>[C:16]1([C:22]2[N:31]=[C:30]([C:32]([N:13]3[CH2:12][CH2:11][C:10](=[O:6])[CH2:15][CH2:14]3)=[O:33])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 20158356HCID 20158356, compoundHCID 178418339Butyllithium

Product 1

HCID 13336381HCID 13336381, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A 1.6M solution of butyllithium in hexane (37 ml) is added, under a nitrogen atmosphere and at 0° C., to 1,4-dioxa-8-azaspiro[4,5]decane (7.5 ml) in anhydrous tetrahydrofuran (30 ml). After 30 minutes, a solution of ethyl 2-phenylquinazoline-4-carboxylate (8 g) in anhydrous tetrahydrofuran (30 ml) is added. After 2 hours at ambient temperature, water is added and the mixture is extracted with methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is taken up in acetone (100 ml) and concentrated hydrochloric acid (20 ml) and the mixture is stirred for 5 hours at ambient temperature.

Workup

  1. waitAfter 2 hours at ambient temperature
  2. extractionthe mixture is extracted with methylene chloride
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-31e101be202e4ee2915e126485a4ca81
Source dataset
uspto-grants-1987_08
Patent number
US04684652

Reaction notes

Loading…