Chloroiodomethane → HCID 69156419, compound

HRID 1624302Notes

Reaction equation

HRID 1624302 reaction equation
[CH2:1]([Zn]CC)C.ClCI.[Si:9]([O:16][CH2:17][CH2:18][C:19](=[CH2:22])[CH2:20][OH:21])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[NH4+].[Cl-]>C(Cl)Cl>[Si:9]([O:16][CH2:17][CH2:18][C:19]1([CH2:20][OH:21])[CH2:1][CH2:22]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 11644ChloroiodomethaneHCID 25517Ammonium ChlorideHCID 11218203HCID 11218203, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 69156419HCID 69156419, compoundYield 97.2%

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 (8 mL) was added neat ClCH2I (0.58 mL, 7.96 mmol) drop wise by syringe. After 1 hour, a solution of 4-(tert-butyldimethylsilyloxy)-2-methylene-butan-1-ol (0.395 g, 1.83 mmol) in CH2Cl2 (4 mL) was added by cannula. After 30 minutes, the reaction mixture was treated with saturated aqueous NH4Cl (10 mL), diluted with CH2Cl2 (12 mL), and warmed to room temperature. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. The crude material was purified by column chromatography on silica gel (9:1 hexanes-ethyl acetate) and provided 0.41 g (97%) of {1-[2-(tert-butyldimethylsilyloxy)-ethyl]-cyclopropyl}-methanol as a colorless oil.

Workup

  1. waitAfter 30 minutes
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 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 (9:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-b357184b70bc4837856eb44b9ca161a9
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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