Diethyl Ether → HCID 57445526, compound

HRID 2238604Notes

Reaction equation

HRID 2238604 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[C:12]1([CH2:18][CH2:19][CH:20]2[C:24]3[CH:25]=[C:26]([CH2:29][OH:30])[CH:27]=[CH:28][C:23]=3[O:22][CH2:21]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)C>C(Cl)Cl>[C:12]1([CH2:18][CH2:19][CH:20]2[C:24]3[CH:25]=[C:26]([CH:29]=[O:30])[CH:27]=[CH:28][C:23]=3[O:22][CH2:21]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 23081965HCID 23081965, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57445526HCID 57445526, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of PCC (3.69 g, 17.10 mmol) in methylene chloride (20 ml), a solution of 3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-yl-methanol (3.32 g, 13.16 mmol) in methylene chloride (100 ml) was added at room temperature. After stirring for 12 h, diethyl ether (300 ml) was added and the black solid precipitated was filtered and washed with diethyl ether several times. The filtrate was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=95/5-9/1) affording 0.202 g of the title compound (67% yield).

Workup

  1. customthe black solid precipitated
  2. filtrationwas filtered
  3. washwashed with diethyl ether several times
  4. concentrationThe filtrate was concentrated under vacuum
  5. customthe residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=95/5-9/1)

Sources & evidence

ORD record
ord-3f71a010d1104ea2beb9844d82768eb3
Source dataset
uspto-grants-2010_05
Patent number
US07718815B2

Reaction notes

Loading…