Hydrochloric Acid → HCID 54116477, compound

HRID 2188361Notes

Reaction equation

HRID 2188361 reaction equation
[CH:1]1([CH:6]2[CH:10]([CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:9]([OH:21])[CH2:8][CH:7]2[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br:30])OCC[O:2]1.Cl>CC(C)=O>[OH:21][CH:9]1[CH2:8][CH:7]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br:30])[CH:6]([CH:1]=[O:2])[CH:10]1[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54083736HCID 54083736, compound

Product 1

HCID 54116477HCID 54116477, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a round-bottomed flask with a magnetic stir bar is placed an amount of the ketal, 1f . To this flask is added a sufficient amount of a mixture of 2 parts acetone to 1 part 1N HCl to bring the ketal completely into solution. This material is stirred by TLC until the starting material is consumed, typically overnight. The crude mixture containing the product 1g is extracted with ether and the ether extract is re-esterified in situ with, preferably, TMS-diazomethane. The organic extracts are concentrated under reduced pressure at 0° C. and used immediately without further purification.

Workup

  1. customIn a round-bottomed flask with a magnetic stir bar is placed
  2. additionTo this flask is added
  3. customis consumed, typically overnight
  4. additionThe crude mixture containing the product 1g
  5. extractionis extracted with ether
  6. extractionthe ether extract
  7. concentrationThe organic extracts are concentrated under reduced pressure at 0° C.
  8. customused immediately without further purification

Sources & evidence

ORD record
ord-f76ffcedb78e455c83ce461d2421583f
Source dataset
uspto-grants-2002_06
Patent number
US06410780B1

Reaction notes

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