Dichloromethane → HCID 66662149, compound

HRID 557864Notes

Reaction equation

HRID 557864 reaction equation
[CH:1]1([CH:6](O)[C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]#[N:17])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)Cl.C(N(S(F)(F)[F:28])CC)C.C([O-])(O)=O.[Na+]>>[CH:1]1([CH:6]([F:28])[C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]#[N:17])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 66661921HCID 66661921, compound

Product 1

HCID 66662149HCID 66662149, compound

Conditions

Temperature
-78 °C

Procedure

1-{4-[Cyclopentyl(hydroxy)methyl]phenyl}cyclopropanecarbonitrile (600.0 mg, 0.002486 mol) was dissolved in methylene chloride (10 mL, 0.2 mol), cooled to −78° C., and to the solution was added diethylaminosulfur trifluoride (0.328 mL, 0.00249 mol) (DAST). The resulting reaction mixture was warmed to rt and stirred at rt for 18 h. The reaction mixture then was poured into ice-water containing NaHCO3 and the resulting mixture was extracted with CH2Cl2 (3×). The combined organic phase was dried over Na2SO4, and concentrated to afford the product.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas warmed to rt
  3. extractionthe resulting mixture was extracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customto afford the product

Sources & evidence

ORD record
ord-d3d4d2bdbcdc41aaa65879c26f5fcc2f
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

Loading…