Hydrochloric Acid → HCID 117687785, compound

HRID 519248Notes

Reaction equation

HRID 519248 reaction equation
[CH3:1][CH:2]1[CH:13]=[C:12]([CH3:14])[CH2:11][CH2:10][C:3]21[C:7](=[O:8])[O:6][C:5](=O)[CH2:4]2.[CH2:15]([Mg]Cl)[CH3:16].Cl.[C:20]1(C)C=CC=C[CH:21]=1>O1CCCC1>[CH2:20]([C:5]1([CH2:15][CH3:16])[CH2:4][C:3]2([CH2:10][CH2:11][C:12]([CH3:14])=[CH:13][CH:2]2[CH3:1])[C:7](=[O:8])[O:6]1)[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 86233933HCID 86233933, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 117687785HCID 117687785, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6,8-Dimethyl-2-oxa-spiro[4.5]dec-7-ene-1,3-dione (prepared as above in EXAMPLE I, 140 g) was fed slowly into an ethyl magnesium chloride (C2H5MgCl) solution in tetrahydrofuran (THF) (2 M, 1.53 L) while the temperature was kept under 25° C. After the feeding was completed, the reaction was aged at room temperature for about an hour. The reaction mixture was then poured into hydrochloric acid (HCl) (2 M) containing ice. Toluene was added. The organic and aqueous layers were shaken in a separatory funnel and separated. The aqueous layer was further washed with toluene. The organic layers were combined and washed with sodium carbonate (Na2CO3) solution until basic. The resulting solution was distilled to afford 3,3-diethyl-6,8-dimethyl-2-oxa-spiro[4.5]dec-7-en-1-one (170 g).

Workup

  1. customwas kept under 25° C
  2. waitthe reaction was aged at room temperature for about an hour
  3. additioncontaining ice
  4. customseparated
  5. washThe aqueous layer was further washed with toluene
  6. washwashed with sodium carbonate (Na2CO3) solution until basic
  7. distillationThe resulting solution was distilled

Sources & evidence

ORD record
ord-995be13a96d44c7a96a438abb8174a2d
Source dataset
uspto-grants-2015_08
Patent number
US09115331B2

Reaction notes

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