Acetyl chloride → 152378-19-3

HRID 1599350Notes

Reaction equation

HRID 1599350 reaction equation
C(Cl)(=O)C.CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:10][CH:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([OH:51])[CH:29]1[O:33][CH:32]([CH:34]2[CH2:38][CH2:37][CH:36]([CH:39]([OH:50])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[O:35]2)[CH2:31][CH2:30]1)[CH2:12][C:13]1[C:14](=[O:19])[O:15][CH:16]([CH3:18])[CH:17]=1)(C)C.C(=O)(O)[O-].[Na+]>CO.C(OCC)C>[OH:10][CH:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([OH:51])[CH:29]1[O:33][CH:32]([CH:34]2[CH2:38][CH2:37][CH:36]([CH:39]([OH:50])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[O:35]2)[CH2:31][CH2:30]1)[CH2:12][C:13]1[C:14](=[O:19])[O:15][CH:16]([CH3:18])[CH:17]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 86751409HCID 86751409, compound

Product 1

HCID 10326164152378-19-3Yield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of acetyl chloride (20 μL) in 400 μL of methanol, a solution of 16a (6.8 mg, 8.2 μmol) in 400 μL of diethyl ether was added at room temperature. The solution was stirred at room temperature until TLC showed that no more starting material was left (about 24 h) . Solid sodium bicarbonate was slowly added until no more gas evolution was observed. The mixture was concentrated under reduced pressure. Diethyl ether (5 mL) was added, and the resulting solution was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification by MPLC (1:3 hexane:ethyl actate) give 1a (4.0 mg, 82%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionDiethyl ether (5 mL) was added
  3. washthe resulting solution was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by MPLC (1:3 hexane:ethyl actate)

Sources & evidence

ORD record
ord-8a176c561d624d26905166a7e11239ac
Source dataset
uspto-grants-1998_04
Patent number
US05739358

Reaction notes

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