Isopropanol → HCID 18966362, compound

HRID 2226119Notes

Reaction equation

HRID 2226119 reaction equation
[CH3:1][C:2]1(C)CC[C:9]2[C:4](=[CH:5][C:6]([C:12]#[C:13][Si](C)(C)C)=[CH:7][CH:8]=2)[S:3]1.[OH-].[K+].[CH:21](O)([CH3:23])[CH3:22]>>[CH3:22][C:21]1([CH3:23])[C:9]2[C:4](=[CH:5][C:6]([C:12]#[CH:13])=[CH:7][CH:8]=2)[S:3][CH2:2][CH2:1]1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 18966360HCID 18966360, compound2×

Product 1

HCID 18966362HCID 18966362, compound

Procedure

To a solution of 1 g (3.6 mmol) of 4,4-dimethyl-7-trimethylsilylethynyl-thio-chroman (Compound 47) in 10 ml of isopropyl alcohol was added 5 ml of 1N KOH solution. The reaction mixture was stirred at room temperature for 18 hours and the isopropanol was then removed under vacuum. The residue was extracted with ether and the ether extracts were combined and washed with dilute HCl solution, water and saturated NaCl solution, and were thereafter dried (MgSO4). The solvent was removed in vacuo to give impure 4,4-dimethyl-7-ethynyl-thiochroman (Compound 48) as a pale yellow oil. This mixture was used in the next step without further purification.

Workup

  1. customthe isopropanol was then removed under vacuum
  2. extractionThe residue was extracted with ether
  3. washwashed with dilute HCl solution, water and saturated NaCl solution
  4. dry with materialwere thereafter dried (MgSO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-34e053492f4c4cb3a8f4baec9dba04c1
Source dataset
uspto-grants-1994_09
Patent number
US05346895

Reaction notes

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