1-Iodododecane → HCID 85863443, compound

HRID 970060Notes

Reaction equation

HRID 970060 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][CH2:7][CH2:8][P:9]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])=[O:10])=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[K+].I[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C1COCC1>[C:4]([CH:6]([CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH3:28])[CH2:7][CH2:8][P:9](=[O:10])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])([O:3][CH2:2][CH3:1])=[O:5]

Participants

5

Reactant 3

HCID 202821-IodododecaneHCID 281201Ethyl 4-(diethoxyphosphoryl)butanoateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 85863443HCID 85863443, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of triethyl 4-phosphonobutyrate (1.00 g, 3.96 mmol) in 1 mL of THF was added to potassium bis(trimethylsilyl)amide (0.5 M in THF, 8.70 ml, 4.36 mmol) at −78° C. After stirring for 1 h at −78° C., 1-iodododecane (1.2 mL, 4.75 mmol) was added dropwise. The reaction was removed from the bath, warmed to rt and stirred for 2 h. The reaction was diluted with ethyl acetate (50 ml), washed with 2 N HCl (50 mL), sat'd NaCl (50 mL), dried and concentrated. Flash chromatography using 3:1 v/v hexane/acetone afforded 610 mg of the title compound: ESI-MS 421.3 (M+H).

Workup

  1. customThe reaction was removed from the bath
  2. temperaturewarmed to rt
  3. stirringstirred for 2 h
  4. additionThe reaction was diluted with ethyl acetate (50 ml)
  5. washwashed with 2 N HCl (50 mL), sat'd NaCl (50 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c07ef4b3d31d46aba520ecac439a69bb
Source dataset
uspto-grants-2007_12
Patent number
US07309721B2

Reaction notes

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