Acetic Anhydride → HCID 12146425, compound

HRID 1883281Notes

Reaction equation

HRID 1883281 reaction equation
[F:1]/[C:2](=[C:6](/[CH3:29])\[CH:7]=[CH:8]\[C:9](\[F:28])=[C:10](/[C:13]1[C:22]([OH:23])=[CH:21][C:20]2[C:19]([CH3:25])([CH3:24])[CH2:18][CH2:17][C:16]([CH3:27])([CH3:26])[C:15]=2[CH:14]=1)\[CH2:11][CH3:12])/[C:3]([OH:5])=[O:4].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([O:23][C:22]1[C:13](/[C:10](/[CH2:11][CH3:12])=[C:9](/[F:28])\[CH:8]=[CH:7]\[C:6](\[CH3:29])=[C:2](/[F:1])\[C:3]([OH:5])=[O:4])=[CH:14][C:15]2[C:16]([CH3:27])([CH3:26])[CH2:17][CH2:18][C:19]([CH3:25])([CH3:24])[C:20]=2[CH:21]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12146424HCID 12146424, compound2×

Product 1

HCID 12146425HCID 12146425, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2Z,4E,6E)-2,6-difluoro-7-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-nona-2,4,6-trienoic acid (Intermediate 22, 108 mg, 0.27 mmol) in pyridine (2 mL) at 0° C. was added acetic anhydride (100 μL, 1.1 mmol). The mixture was stirred for 4 h while warmed to ambient temperature. The reaction was quenched with aqueous Na2CO3, stirred for 30 min, acidified with 1M HCl and extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10%→50% EtOAc-hexane) to give the title compound as a yellow solid (82 mg, 69%).

Workup

  1. customThe reaction was quenched with aqueous Na2CO3
  2. stirringstirred for 30 min
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel (10%→50% EtOAc-hexane)

Sources & evidence

ORD record
ord-44a74194caf94a2194b15a4593d9d45b
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

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