1-Iodopentane → HCID 19382490, compound

HRID 2400204Notes

Reaction equation

HRID 2400204 reaction equation
[Br:1][C:2]1[CH:36]=[CH:35][C:5]([O:6][CH2:7][CH:8]([OH:34])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.I[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>C1COCC1.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH:8]([O:34][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)[CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 123351-IodopentaneHCID 19382485HCID 19382485, compound

Product 1

HCID 19382490HCID 19382490, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A mixture of the product (0.57 g) of Step 3, 0.3 mL of 1-iodopentane and 80 mg of Nail in 20 ml of 1:1 THF/DMF was refluxed for 4 hrs. The mixture was then quenched with 5 mL of MeOH, 20 mL of Sat. NH4Cl, and extracted with 50 mL of Et2O. The extract was dried over NaSO4 and concentrated. The residue was purified by flash chromatography eluted with EtOAc and hexanes (7:1) to give 0.6 g of the title compound.

Workup

  1. temperaturewas refluxed for 4 hrs
  2. customThe mixture was then quenched with 5 mL of MeOH, 20 mL of Sat. NH4Cl
  3. extractionextracted with 50 mL of Et2O
  4. dry with materialThe extract was dried over NaSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluted with EtOAc and hexanes (7:1)

Sources & evidence

ORD record
ord-a1d00aae05974982bf38c00a32b72788
Source dataset
uspto-grants-1995_09
Patent number
US05453443

Reaction notes

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