Dimethyl 3,3'-(((3-formylphenyl)methylene)bis(sulfanediyl))dipropanoate → HCID 53900955, compound

HRID 1032324Notes

Reaction equation

HRID 1032324 reaction equation
[Br-].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:8][C:7]=2[CH:31]=1.[Li]CCCC.[CH:37]([C:39]1[CH:40]=[C:41]([CH:45]([S:53][CH2:54][CH2:55][C:56]([O:58][CH3:59])=[O:57])[S:46][CH2:47][CH2:48][C:49]([O:51][CH3:52])=[O:50])[CH:42]=[CH:43][CH:44]=1)=O>O1CCCC1.CCCCCC>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]=[CH:37][C:39]3[CH:40]=[C:41]([CH:45]([S:46][CH2:47][CH2:48][C:49]([O:51][CH3:52])=[O:50])[S:53][CH2:54][CH2:55][C:56]([O:58][CH3:59])=[O:57])[CH:42]=[CH:43][CH:44]=3)=[N:8][C:7]=2[CH:31]=1

Participants

6

Reactant 3

HCID 10021188Dimethyl 3,3'-(((3-formylphenyl)methylene)bis(sulfanediyl))dipropanoateHCID 23055263(5 Chlorobenzoxazol-2-yl methyl)triphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 53900955HCID 53900955, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of phosphonium bromide (780 mg) (Step 4) in tetrahydrofuran (THF) (8 mL) at -78° was added dropwise 1 eq. of n-BuLi in hexane. The solution was stirred at -78° for 15 min. Then (545 mg) of the aldehyde (Step 1) in THF (4 mL) was added dropwise and the reaction mixture was stirred at -78° for 1 hour. The reaction mixture was poured into pH 7 buffer, extracted with ethyl acetate, dried and evaporated. The residue was chromatographed on a column of SiO2 using 10:1 toluene/ethyl acetate to afford the title compound, m.p. 66°-67° C.

Workup

  1. stirringthe reaction mixture was stirred at -78° for 1 hour
  2. additionThe reaction mixture was poured into pH 7 buffer
  3. extractionextracted with ethyl acetate
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on a column of SiO2 using 10:1 toluene/ethyl acetate

Sources & evidence

ORD record
ord-79529cb249c848a6b8e08b4fdf46a378
Source dataset
uspto-grants-1990_09
Patent number
US04957932

Reaction notes

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