Diiodomethane → HCID 24777030, compound

HRID 2177033Notes

Reaction equation

HRID 2177033 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=O.ICI.[Sm].O1CC[CH2:18][CH2:17]1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2([OH:7])[CH2:18][CH2:17]2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6346DiiodomethaneHCID 8028Tetrahydrofuran2×HCID 17946Methyl 3-chlorobenzoateHCID 23951Samarium

Product 1

HCID 24777030HCID 24777030, compound

Conditions

Temperature
-10 °C

Procedure

A solution of methyl 3-chlorobenzoate (0.27 g, 1.58 mmol) and diiodomethane) in anhydrous tetrahydrofuran was added slowly to a vigorously stirred and heated (50° C.) slurry of samarium powder (1.0 g, 6.65 mmol) in tetrahydrofuran over 1.5 hours. After complete addition, the reaction mixture was stirred for 1 hour, than cooled (−10° C.), quenched with 1 N hydrochloric acid over 30 min. The reaction mixture was extracted with ether, dried, filtered and concentrated. Purification by silica gel chromatography (1:1 hexanes in dichloromethane) afford 100 mg of 1-(3-chlorophenyl)cyclopropanol.

Workup

  1. additionAfter complete addition
  2. stirringthe reaction mixture was stirred for 1 hour
  3. customquenched with 1 N hydrochloric acid over 30 min
  4. extractionThe reaction mixture was extracted with ether
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (1:1 hexanes in dichloromethane)

Sources & evidence

ORD record
ord-3a7c145355194d989db83651c3258512
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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