Acetic Anhydride → HCID 68822490, compound

HRID 2378509Notes

Reaction equation

HRID 2378509 reaction equation
[OH:1][C:2]12[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2.[CH3:19][C:20](OC(C)=O)=[O:21].CC1C=CC(S(O)(=O)=O)=CC=1.O>[NH4+].[Cl-]>[C:20]([O:1][C:2]12[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)(=[O:21])[CH3:19]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 521998p-Toluenesulfonic acid monohydrateHCID 67491946HCID 67491946, compound

Product 1

HCID 68822490HCID 68822490, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

2.5 g (10 mmol) of (16) were added to a mixture of 4 g (40 mmol) Ac2O and 95 mg (0.5 mmol) pTsOH.H2O at 0° C. After stirring for 1 hour at 0° C. the mixture was warmed up to room temperature. After 60 minutes, the reaction mixture was poured into 10 g of ice and 10 ml of a saturated aqueous NH4Cl solution. After extraction with 150 ml diethyl ether the combined organic phases were washed (saturated aqueous NaHCO3 and NaCl solution), dried (Na2SO4) and 1 ml Et3N were added. The solvent was evaporated. Flash chromatography, using SiO2 (300 g) and n-pentane/EtOAc/Et3N=95/4/1 as eluent, afforded 1.31 g (4.4 mmol, yield: 44%) of (28).

Workup

  1. temperaturewas warmed up to room temperature
  2. waitAfter 60 minutes
  3. extractionAfter extraction with 150 ml diethyl ether the combined organic phases
  4. washwere washed (saturated aqueous NaHCO3 and NaCl solution)
  5. dry with materialdried (Na2SO4) and 1 ml Et3N
  6. additionwere added
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3c29cb687c6947d288635190ce29eb8b
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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