1-Iodononane → HCID 19063065, compound

HRID 482499

Reaction equation

HRID 482499 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:14]=[C:15]([C:20]#[C:21][C:22]4[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=4)[CH:16]=[CH:17][C:18]=3[OH:19])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.I[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CN(C=O)C>[C:3]12([C:13]3[CH:14]=[C:15]([C:20]#[C:21][C:22]4[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=4)[CH:16]=[CH:17][C:18]=3[O:19][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2

Participants

5

Reactant 3

HCID 202751-IodononaneHCID 24758Sodium hydrideHCID 19063002HCID 19063002, compound

Product 1

HCID 19063065HCID 19063065, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

75 mg (2.6 mmol) of sodium hydride (80% in oil) and 10 ml of DMF were introduced into a three-necked flask under a stream of nitrogen. A solution of 1 g (2.6 mmol) of methyl 4-[3-(1-adamantyl)-4-hydroxyphenylethynyl]benzoate dissolved in 70 ml of DMF was added dropwise and stirring was carried out at room temperature until gas evolution had ceased. 610 μl (3.1 mmol) of 1-iodononane were then added dropwise and stirring was carried out at room temperature for four hours. The reaction mixture was poured into ice-cold water and extracted with ethyl ether and the organic phase was separated by settling, dried over magnesium sulphate and evaporated.

Workup

  1. additionwas added dropwise
  2. customwas carried out at room temperature until gas evolution
  3. stirringstirring
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionextracted with ethyl ether
  6. customthe organic phase was separated
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-67c74de11e5e4562b4be5c53edc1b080
Source dataset
uspto-grants-1998_08
Patent number
US05798354

Linked notes

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