Diisopropyl Ether → HCID 15240201, compound

HRID 1492726Notes

Reaction equation

HRID 1492726 reaction equation
[OH:1][C@H:2]1[C@H:7]([OH:8])[C@@H:6]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[O:5][C:3]1=[O:4].[H][H].CCCCCC.C(OC(C)C)(C)C>C(O)C>[OH:1][C@H:2]1[C@H:7]([OH:8])[C@H:6](/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[O:5][C:3]1=[O:4]

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 8058HexaneHCID 15240200HCID 15240200, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15240201HCID 15240201, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.924 g (7.58 mmol) of the compound (15) obtained in step e were dissolved in 20 ml of ethanol, 40 mg of 5 wt % Pd--CaCO3 /Pb (Lindlar catalyst) were added thereto, and the resultant solution was strongly stirred in a hydrogen flow. The solid product in the reaction solution was filtered, and the solvent was distilled at a reduced pressure, thereby obtaining a colorless solid product. This solid product was recrystallized using 50 ml of a hexane/isopropyl ether solution mixture obtained by mixing hexane with isopropyl ether at a mixing ratio of 20:30 to obtain 1.45 g of a colorless fibrous compound (16) (yield:74.6%). The physical data of the resultant compound (16) were as follows.

Workup

  1. addition40 mg of 5 wt % Pd--CaCO3 /Pb (Lindlar catalyst) were added
  2. filtrationThe solid product in the reaction solution was filtered
  3. distillationthe solvent was distilled at a reduced pressure
  4. customobtaining a colorless solid product
  5. customThis solid product was recrystallized
  6. customobtained

Sources & evidence

ORD record
ord-e33c4299fd90410e8b427e7f8bc84df1
Source dataset
uspto-grants-1994_12
Patent number
US05374744

Reaction notes

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