Iodine → HCID 85962995, compound

HRID 1516119Notes

Reaction equation

HRID 1516119 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[I:20]I>C1COCC1>[I:20][C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 807Iodine2×HCID 85962992HCID 85962992, compound2×

Product 1

HCID 85962995HCID 85962995, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Nonadeca-1,8,10-triyne (0.802 g, 3.133 mmol) and anhydrous THF (96 mL) was cooled to −78° C. in a dry flask under nitrogen. LiN[Si(CH3)]2 (LHMDS) in THF (3.76 mmol) was added to the reaction mix slowly via dry syringe. In a separate flask I2 (9.55 g, 3.76 mmol) was dissolved in dry THF (20 mL). The iodine solution was added dropwise to the nonadeca-1,8,10-triyne solution until reaction completion (notably becoming orange-red). The reaction was stirred for 30 min, and slowly warmed to room temperature. The reaction was extracted with diethyl ether and 1M K2S2O3. The organic phase was dried over anhydrous MgSO4, and concentrated by evaporation to yield 1-iodo-nonadeca-1,8,10-triyne (0.93 g, 2.45 mmol). GC/MS showed no starting material remaining. 79% yield; 1H NMR (CDCl3) δ 2.15-2.33 (m, 6H, CH2—C≡C), 1.48 (m, 6H, CH2—C—C≡C), 1.33-1.39 (m, 2H, CH2—CH2—CH3), 1.28 (m, 10H, C—CH2—C), 0.85 (t, 3H, CH3).

Workup

  1. additionmix slowly
  2. customvia dry syringe
  3. extractionThe reaction was extracted with diethyl ether and 1M K2S2O3
  4. dry with materialThe organic phase was dried over anhydrous MgSO4
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-6f6598b60c0d408199345294896f9c0f
Source dataset
uspto-grants-2012_07
Patent number
US08227035B2

Reaction notes

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