Dichloromethane → HCID 54436487, compound

HRID 280093Notes

Reaction equation

HRID 280093 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(Cl)Cl.[CH3:25][C:26]1[C:27]([Si:35]([CH3:43])([CH3:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:28]([C:31]([CH3:34])=[CH:32][CH:33]=1)[CH2:29][OH:30]>C(OCC)C>[CH3:25][C:26]1[C:27]([Si:35]([CH3:43])([CH3:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:28]([C:31]([CH3:34])=[CH:32][CH:33]=1)[CH:29]=[O:30]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724130Cornforth reagentHCID 54356322HCID 54356322, compound

Product 1

HCID 54436487HCID 54436487, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyridinium dichromate (9.24 g, 1.8 equivalents) was added to a methylene chloride solution of the benzyl alcohol product of step (q), above, at room temperature. The reaction was stirred for 24 hours, then diluted with diethyl ether and filtered. The filtrate was concentrated on a rotary evaporator and the residual oil was taken up in MTBE and washed with 2N hydrochloric acid, aqueous NaHCO3, brine, treated with charcoal, dried and concentrated on a rotary evaporator to give the product of this step as a pale yellow oil. The product was distilled under reduced pressure (~0.5 mm Hg) using a Kugelrohr apparatus to give 3.3 g of refined product as a clear oil.

Workup

  1. customat room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated on a rotary evaporator
  4. washwashed with 2N hydrochloric acid, aqueous NaHCO3, brine
  5. additiontreated with charcoal
  6. customdried
  7. concentrationconcentrated on a rotary evaporator
  8. customto give the product of this step as a pale yellow oil
  9. distillationThe product was distilled under reduced pressure (~0.5 mm Hg)

Sources & evidence

ORD record
ord-d55757a243a14fa5845ed3ea397b56ac
Source dataset
uspto-grants-1986_05
Patent number
US04588715

Reaction notes

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