Sulfuric Acid → HCID 10911826, compound

HRID 1780052Notes

Reaction equation

HRID 1780052 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[OH:13][C@H:14]([CH3:27])[CH2:15][C:16]#[C:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+]>O>[C:1]([O:13][C@H:14]([CH3:27])[CH2:15][C:16]#[C:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22872725HCID 22872725, compound

Product 1

HCID 10911826HCID 10911826, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Next, acetic anhydride (23.6 ml, 0.25 mole) and sulfuric acid (0.13 ml) were added to stirred 5-(R)-hydroxy-1-benzyloxy-2-hexyne (34 g, 0.17 mole), prepared above, at 25° C., and the reaction was heated to 60° C. for 20 hours. Water (100 ml) was added, followed by solid sodium bicarbonate (33 g, 0.40 mole) in portions. The reaction mixture was extracted with ethyl acetate (80 ml), the solvent dried (magnesium sulfate) and evaporated to afford 5-(R)-acetoxy-1-benzyloxy-2-hexyne (41.1 g, 99% yield) as a brown oil.

Workup

  1. customprepared above, at 25° C.
  2. extractionThe reaction mixture was extracted with ethyl acetate (80 ml)
  3. dry with materialthe solvent dried (magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-88bac824526949e1938942e7a7bb1d07
Source dataset
uspto-grants-1997_05
Patent number
US05629423

Reaction notes

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