Iodine → 3,6,9,34,37,40-Hexaoxa-21,22-dithiadotetracontane-1,42-diol

HRID 890916Notes

Reaction equation

HRID 890916 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22].[OH-:23].[Na+].II.C(Cl)Cl>C1COCC1>[OH:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][S:1][S:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:23][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22]

Participants

6

Reactant 4

HCID 807IodineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 45920432-(2-{2-[(11-Sulfanylundecyl)oxy]ethoxy}ethoxy)ethan-1-ol

Product 1

HCID 713625613,6,9,34,37,40-Hexaoxa-21,22-dithiadotetracontane-1,42-diolYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{2-[2-(11-mercapto-undecyloxy)-ethoxy]-ethoxy}-ethanol (145 mg, 0.43 mmol) dissolved in 5 mL of THF was added 1 mL of a NaOH solution (0.1 M), followed by iodine (5 crystals). The solution was stirred at room temperature for 24 h and added to 20 mL of CH2Cl2. After the solution was rinsed with H2O (2×5 mL), the organics were dried over MgSO4 and concentrated. The crude residue was purified by flash chromatography (CH2Cl2/MeOH, 20:1, v/v) to afford 78 mg (54%) of 2. 1H NMR 400 MHz (CDCl3) d 3.72–3.52 (br, 24H), 3.44 (t, J=7.2 Hz, 4H), 2.66 (t, J=7.0 Hz, 2H), 2.41 (br s, 2H), 1.65 (m, 4H), 1.57 (m, 4H), 1.41–1.20 (br, 28H).

Workup

  1. washAfter the solution was rinsed with H2O (2×5 mL)
  2. dry with materialthe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography (CH2Cl2/MeOH, 20:1

Sources & evidence

ORD record
ord-0234f148dc214958a0a470bd76776325
Source dataset
uspto-grants-2006_02
Patent number
US07001740B2

Reaction notes

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