Hydrogen Sulfide → 2-Methyl-1-sulfanylheptan-2-OL

HRID 371334Notes

Reaction equation

HRID 371334 reaction equation
[SH2:1].[CH3:2][C:3]1([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[O:5][CH2:4]1.C(NC(C)C)(C)C>O1CCCC1.CCOCC>[SH:1][CH2:4][C:3]([CH3:2])([OH:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 402Hydrogen SulfideHCID 7912DiisopropylamineHCID 5590732-Methyl-2-pentyloxirane

Product 1

HCID 135068602-Methyl-1-sulfanylheptan-2-OL

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Hydrogen sulfide gas was bubbled into a solution of 5 (3.84 g, 30 mmol) in tetrahydrofuran (30 mL) containing diisopropylamine (21 mL, 150 mmol) for one hour and the reaction mixture was stirred at room temperature for 68 hours. It was diluted with ether and washed with 10% aqueous hydrogen chloride, saturated sodium bicarbonate solution, and saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo; 1.2 g of 1-mercapto-2-methylheptan-2-ol 6 was obtained after HPLC purification. IR (neat): 3600-3200 cm-1 (br); PMR (CDCl3): δ 2.67 (s, 1H), 2.57 (s, 1H), 2.17 (s, 1H), 1.70-1.20 (m, 9H), 1.22 (s, 3H), and 0.90 (t, 3H).

Workup

  1. washwashed with 10% aqueous hydrogen chloride, saturated sodium bicarbonate solution, and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-52caa06b358c4e88b6317301624a9963
Source dataset
uspto-grants-1985_07
Patent number
US04530933

Reaction notes

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