Iodine → HCID 58237933, compound

HRID 1192918Notes

Reaction equation

HRID 1192918 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].II.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1.[Zn]>[Cl:1][CH2:2][CH2:3][C:4]([OH:5])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 807IodineHCID 7748Ethyl bromoacetateHCID 702953-Chloropropiophenone

Product 1

HCID 58237933HCID 58237933, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-chloro-1-phenylpropan-1-one (10 g, 0.059 mol) and active Zinc power (19 g, 0.295 mol) in THF (200 mL) was added iodine (9 g, 0.035 mol), then ethyl bromoacetate (20 g, 0.118 mol) was added dropwise at rt. The formed mixture was heated to reflux for 30 min. The reaction was quenched with water, and the mixture was filtered through a celite pad. The filtrate was extracted with EtOAc. The organic phase was dried over Na2SO4, and concentrated to give the crude product, which was purified by column chromatography to afford ethyl 5-chloro-3-hydroxy-3-phenylpentanoate (8.0 g, 53%). 1H NMR (CDCl3): δ=1.02 (t, 3H), 2.13-2.28 (m, 2H), 2.73 (d, 1H), 2.90 (d, 1H), 3.11 (1, 2H), 3.54 (m, 1H), 3.94 (q, 2H), 7.18 (m, 1H), 7.29 (m, 4H).

Workup

  1. temperatureThe formed mixture was heated
  2. temperatureto reflux for 30 min
  3. customThe reaction was quenched with water
  4. filtrationthe mixture was filtered through a celite pad
  5. extractionThe filtrate was extracted with EtOAc
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-fc01b31a9f50442cad96f6827a1a1ff6
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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