Water → HCID 22858010, compound

HRID 2260418Notes

Reaction equation

HRID 2260418 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([SH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])[CH3:3].[O-]CC.[Na+].[CH:20]12[O:26][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]2.O>C(O)C>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([S:15][C@@H:20]2[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]2[OH:26])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 9246Cyclohexene oxideHCID 2723922Sodium ethoxideHCID 14795713HCID 14795713, compound

Product 1

HCID 22858010HCID 22858010, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Bis(1,1-dimethylethyl)benzenethiol (Example 2) (5.0 g, 0.0225 moles) was added to freshly prepared sodium ethoxide (0.0230 moles) in absolute ethyl alcohol (50 ml). After stirring for 1 hour, cyclohexene oxide (2.2 g; 0.0225 moles) was added by syringe over 5 minutes, and the reaction mixture was stirred for 60 hours at room temperature. Water (100 ml) was added, and the reaction mixture was extracted twice with 75 ml of ethyl acetate. The combined ethyl acetate extracts were washed with brine (50 ml), dried over sodium sulfate, filtered and concentrated to give the title product as a yellow solid, which was recrystallized from cold pentane. The structure assignment was supported by NMR spectroscopy. The title compound was used in Example 4.

Workup

  1. stirringthe reaction mixture was stirred for 60 hours at room temperature
  2. extractionthe reaction mixture was extracted twice with 75 ml of ethyl acetate
  3. washThe combined ethyl acetate extracts were washed with brine (50 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e6a8cbbc022a45478bcb1ab0f86b0191
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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