5-Phenylthiophene-2-carbaldehyde → HCID 54508132, compound

HRID 414585Notes

Reaction equation

HRID 414585 reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH:6]1([CH2:12][N:13]([CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)P(OC)(OC)=O)[C:14](=[O:16])[O-:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH:30]([C:32]1[S:33][C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][CH:36]=1)=O>CCCCCC.O1CCCC1>[CH:6]1([CH2:12][N:13]([C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:30][C:32]2[S:33][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:35][CH:36]=2)[C:14](=[O:16])[O:15][CH2:1][CH3:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 1770535-Phenylthiophene-2-carbaldehydeHCID 86742626HCID 86742626, compoundHCID 178418339Butyllithium

Product 1

HCID 54508132HCID 54508132, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere n-butyllithium (1.3 mL of a 2.5M solution in hexane) was added to a stirred, cold (-78° C.) solution of 1.15 gram (0.00293 mole) of N-cyclohexylmethyl-N-[phenyl(dimethoxyphosphinyl)methyl]carbamate in approximately 20 mL of tetrahydrofuran. This mixture was stirred for about 30 minutes at -78° C. after which 2-formyl-5-phenylthiophene (0.51 gram, 0.0027 mole) was added. The mixture was allowed to gradually warm to room temperature and stir for four hours. The reaction mixture was quenched with dilute hydrochloric acid and was then extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and filtered through celite. The filtrate was evaporated under reduced pressure to yield 0.6 gram of ethyl N-cyclohexylmethyl-N-[1-phenyl-2-(5-phenyl-2-thienyl)ethene-1-yl]carbamate as a red gel.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with dilute hydrochloric acid
  3. extractionwas then extracted with chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered through celite
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3219b999707a43618c9506ff3450bb22
Source dataset
uspto-grants-1988_12
Patent number
US04792567

Reaction notes

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