Diethyl Ether → HCID 13456734, compound

HRID 746150Notes

Reaction equation

HRID 746150 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7]2[O:8][CH2:9][C:10]([CH3:13])([CH3:12])[N:11]=2)=[CH:3][CH:2]=1.C([Li])CCC.[CH3:25][S:26]SC.CCOCC>O1CCCC1.O>[CH3:25][S:26][C:3]1[CH:2]=[C:1]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][C:4]=1[C:7]1[O:8][CH2:9][C:10]([CH3:12])([CH3:13])[N:11]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 12232Dimethyl DisulfideHCID 10131201HCID 10131201, compoundHCID 178418339Butyllithium

Product 1

HCID 13456734HCID 13456734, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 13.3 g of the biphenyl oxazoline of Example 1 in 210 mL tetrahydrofuran (THF) was treated with 36 mL of 1.6M n-butyllithium in hexanes at <-70° under nitrogen atmosphere. The mixture was kept at ca. -40° for 50 min., then 5.2 mL methyl disulfide was added and the mixture slowly warmed to room temperature. After 2 days the solution was poured into ether and water, the organic phase was washed successively with saturated sodium bicarbonate solution brine, then dried and evaporated. Trituration of the residue with n-chlorobutane plus hexanes gave 10.9 g of the title compound, mp 93°-95°.

Workup

  1. washthe organic phase was washed successively with saturated sodium bicarbonate solution brine
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-4e514c7a4d5047e9a04685e5cce904d9
Source dataset
uspto-grants-1986_07
Patent number
US04602942

Reaction notes

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