Hydrochloric Acid → 2-(4,4-Dimethyl-thiochroman-7-yl)-heptan-1-ol

HRID 899278Notes

Reaction equation

HRID 899278 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([C:12](=[CH2:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1.[OH-:20].[Na+].OO.Cl>C1COCC1.O>[CH3:19][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][C:8]([CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:18][OH:20])=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22640670HCID 22640670, compound

Product 1

HCID 226406822-(4,4-Dimethyl-thiochroman-7-yl)-heptan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,4-dimethyl-7-(1-methylene-hexyl)-thiochroman (0.939 g, 3.42 mmole) in 15 mL of THF at 0° C., was treated with 3.42 mL of 1M BH3.THF complex. The reaction mixture was stirred at room temperature for three hours and then cooled to 0° C. The mixture was treated successively with 0.59 mL of water, 0.67 mL of 3M sodium hydroxide and 0.67 mL of 30% hydrogen peroxide. The reaction mixture was stirred at room temperature for two hours and then diluted with 20 mL of water. The pH was adjusted to 4.0 with 10% HCl and then extracted with three 25 mL portions of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes) to yield 0.532 g of 2-(4,4-dimethyl-thiochroman-7-yl)-heptan-1-ol as a colorless oil.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe reaction mixture was stirred at room temperature for two hours
  3. extractionextracted with three 25 mL portions of ether
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow oil
  8. customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-477334167bd240e8a098e82b1c5f5ba8
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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