Chloroiodomethane → HCID 69178338, compound

HRID 899792Notes

Reaction equation

HRID 899792 reaction equation
[CH2:1]([Zn]CC)C.ClCI.[OH:9][CH2:10][C:11](=[CH2:25])[CH2:12][CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].[NH4+].[Cl-]>C(Cl)Cl>[O:24]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22](=[O:23])[N:14]1[CH2:13][CH2:12][C:11]1([CH2:10][OH:9])[CH2:1][CH2:25]1

Participants

6

Reactant 4

HCID 11644ChloroiodomethaneHCID 25517Ammonium ChlorideHCID 69177739HCID 69177739, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 69178338HCID 69178338, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a cold (0° C.), stirred solution of diethyl zinc (1.0 M in hexanes, 4.0 mL, 4.0 mmol) in CH2Cl2 (10 mL) was added neat ClCH2I (0.59 mL, 8.10 mmol) drop wise by syringe. After 30 minutes, a solution of 2-(3-Hydroxymethyl-but-3-enyl)-isoindole-1,3-dione (0.456 g, 1.97 mmol) in CH2Cl2 (6 mL) was added by cannula. After 60 minutes, the reaction mixture was treated with saturated aqueous NH4Cl (20 mL), diluted with CH2Cl2 (20 mL), and warmed to room temperature. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated. The crude material was purified by column chromatography on silica gel (1:1 hexanes-ethyl acetate) and provided 0.31 g (64%) of 1-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclopropane-methanol as a white solid. 1H NMR (CDCl3) δ 0.31-0.34 (m, 2H), 0.38-0.43 (m, 2H), 1.75 (t, 2H, J=6.9 Hz), 3.54 (s, 2H), 3.90(t, 2H, J=6.6 Hz), 7.70-7.73 (m, 2H), 7.81-7.85 (m, 2H);

Workup

  1. waitAfter 60 minutes
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude material was purified by column chromatography on silica gel (1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-26ea1c3b649044d4806564dc3f93d0cb
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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