Iodoethane → HCID 57827623, compound

HRID 1693189Notes

Reaction equation

HRID 1693189 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([OH:25])[CH2:22][CH:23]=[CH2:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26](I)[CH3:27].[H-].[Na+]>C1COCC1>[C:14]([Si:1]([O:18][CH2:19][CH2:20][CH:21]([O:25][CH2:26][CH3:27])[CH2:22][CH:23]=[CH2:24])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:16])([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 24758Sodium hydrideHCID 14761231HCID 14761231, compound

Product 1

HCID 57827623HCID 57827623, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 1-(tert-butyl-diphenylsilanyloxy)-5-hexen-3-ol (Tetrahedron, 57, 4023-4034 (2001)) (5.0 g) and ethyl iodide (2.03 mL) in THF (10 mL) was added dropwise to a suspension of sodium hydride (60%, 1.85 g) in THF (40 mL) at 50° C. over 10 minutes. The reaction solution was stirred at 50° C. for one hour. Ethyl iodide (6.0 mL) was added to the solution at 50° C., and the mixture was stirred at 60° C. for 1.5 hours. The reaction solution was returned to room temperature and poured into ice water, followed by extraction with ethyl acetate. The extract was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain the title compound (4.1 g).

Workup

  1. stirringthe mixture was stirred at 60° C. for 1.5 hours
  2. customwas returned to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f8a98faf370a41ed950dc2625f39eed7
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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