HCID 12985406, compound → HCID 11265620, compound

HRID 2184666Notes

Reaction equation

HRID 2184666 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:20][Br:21])[CH2:9][C:10]([O:12]CC1C=CC=CC=1)=[O:11]>O1CCCC1.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:20][Br:21])[CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 12985406HCID 12985406, compound

Product 1

HCID 11265620HCID 11265620, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 3 (73 mg, 0.20 mmole) was dissolved in tetrahydrofuran (3 mL) and 10% palladium on charcoal (65 mg) was added. The mixture was flushed thrice with nitrogen, thrice with hydrogen, and then stirred under hydrogen for 45 min. The mixture was filtered through Celite, the Celite was rinsed with ethyl acetate (10 mL), and the combined filtrates were evaporated to give 3-[2-tetrahydropyranyloxy]4-bromobutanoic acid as a colourless oil, 54 mg (98%). IR (neat): 1715 cm−1. Mass spectrum (CI, m/z): 267, 269 (M+1, M+3).

Workup

  1. customThe mixture was flushed thrice with nitrogen, thrice with hydrogen
  2. filtrationThe mixture was filtered through Celite
  3. washthe Celite was rinsed with ethyl acetate (10 mL)
  4. customthe combined filtrates were evaporated

Sources & evidence

ORD record
ord-959b25f291d144ff837a466b2443d2b9
Source dataset
uspto-grants-2002_06
Patent number
US06399600B1

Reaction notes

Loading…