Dimethyl Sulfide → HCID 19103244, compound

HRID 483820Notes

Reaction equation

HRID 483820 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1Br.[Li]CCCC.S(C)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1.CCCCCC>[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 1068Dimethyl Sulfide2×HCID 7412Benzoyl chlorideHCID 18398840HCID 18398840, compoundHCID 178418339Butyllithium

Product 1

HCID 19103244HCID 19103244, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-bromo-5-benzyloxy benzaldehyde dimethyl acetal (Tet. Lett., 22, 5027 (1981)) (52.2 g) in THF (600 mL), cooled to -78° C., was added dropwise a solution of n-BuLi (78 ml, 2.1M) in hexane. After 15 min. CuBr.SMe2 (32 g) was added in 3 portions. The reaction mixture was stirred at -78° C. until CuBr.SMe2 was dissolved (approx. 1 hr.), then benzoyl chloride (20 mL) was added dropwise. The cooling bath was removed and the reaction mixture was stirred at room temperature over night and was quenched with a saturated NH4Cl solution. The organic phase was diluted with Et2O, washed with H2O (3×), brine, dried (MgSO4) and evaporated to afford the title compound which was used as such for the next step.

Workup

  1. customThe cooling bath was removed
  2. customwas quenched with a saturated NH4Cl solution
  3. additionThe organic phase was diluted with Et2O
  4. washwashed with H2O (3×), brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-95e1e1c17ff04f638c8693573cb73066
Source dataset
uspto-grants-1993_07
Patent number
US05227399

Reaction notes

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