Diphenyl sulfide → 3-[3-Acetoxy-4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-propionic acid ethyl ester

HRID 2070601Notes

Reaction equation

HRID 2070601 reaction equation
[CH2:1]([O:3][C:4](=[O:29])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH2:24][CH2:23][CH2:22][C:17]3([CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:16]=2)=[C:9]([O:25][C:26](=[O:28])[CH3:27])[CH:8]=1)[CH3:2].C1(SC2C=CC=CC=2)C=CC=CC=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH2:24][CH2:23][CH2:22][C:17]3([CH2:18][CH2:19][CH2:20][CH2:21]3)[CH:16]=2)=[C:9]([O:25][C:26](=[O:28])[CH3:27])[CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 8766Diphenyl sulfideHCID 57771492HCID 57771492, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 577714653-[3-Acetoxy-4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-propionic acid ethyl esterYield 76.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (E)-3-[3-acetoxy-4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-acrylic acid ethyl ester (0.43 g) obtained in Step 4 in ethyl acetate (8 mL) were added 10% palladium carbon (86 mg) and a 0.1M ethyl acetate solution of diphenyl sulfide (1.08 mL), followed by stirring under increased pressure (0.4 MPa) in an atmosphere of hydrogen at room temperature for 6 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (hexane→ethyl acetate:hexane (volume ratio)=1:19 to 1:9) to give 3-[3-acetoxy-4-(spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-propionic acid ethyl ester (0.332 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (hexane→ethyl acetate:hexane (volume ratio)=1:19 to 1:9)

Sources & evidence

ORD record
ord-c754d92fee684baaa248b6c3a175e98f
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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