(E)-10-Iodo-2-(phenylmethylidene)deca-3,9-diyn-1-ol → (E)-10-Iodo-2-(phenylmethylidene)deca-3,9-diyn-1-al

HRID 1936915Notes

Reaction equation

HRID 1936915 reaction equation
[I:1][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9]/[C:10](=[CH:13]\[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)/[CH2:11][OH:12].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[I:1][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9]/[C:10](=[CH:13]\[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)/[CH:11]=[O:12]

Participants

5

Reactant 2

HCID 12022750(E)-10-Iodo-2-(phenylmethylidene)deca-3,9-diyn-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 11348993(E)-10-Iodo-2-(phenylmethylidene)deca-3,9-diyn-1-alYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 4 (399.4 mg, 1.10 mmol) in dry CH2Cl2 (50 mL) cooled at 0° C. in an ice-water bath was added PCC (591.3 mg, 2.74 mmol) followed by stirring at room temperature for 2 hours. The reaction mixture was diluted with Et2O and filtered through a short silica gel plug with rinsing by EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 17 percent EtOAc in hexane) to give 296.6 mg (75 percent) of Compound 5: pale yellow oil; Rf=0.36 (17 percent EtOAc in hexane); IR (neat) 2942, 2230, 1690, 1596, 1450, 1324, 1180 cm−1; 1H NMR (300 MHz, CDCl3) δ9.55 (s, 1H), 8.10-8.04 (m, 2H), 7.48-7.44 (m, 3H), 7.42 (s, 1H), 2.60 (td, J=6.66, 2.46 Hz, 2H), 2.44 (t, J=6.75, 2H), 1.83-1.66 (m, 4H); 13C NMR (75 MHz, CDCl3) δ192.4, 151.9, 134.8, 132.1, 131.0, 129.4, 124.0, 103.3, 94.7, 75.4, 28.3, 28.0, 21.1, 20.3, −5.9; MS (+CI) m/z (relative intensity) 363 (M+H+, 40), 207 (100); HRMS (+EI) calcd for C17H15IO 362.0168 (M+), found 362.0107.

Workup

  1. filtrationfiltered through a short silica gel plug
  2. washwith rinsing by EtOAc
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash column chromatography (silica gel, 17 percent EtOAc in hexane)

Sources & evidence

ORD record
ord-3d4d2a1529574f7f967cc35e8c594511
Source dataset
uspto-grants-2002_05
Patent number
US06391916B1

Reaction notes

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