tert-Butanol → HCID 57424231, compound

HRID 2377368Notes

Reaction equation

HRID 2377368 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]([OH:14])=[O:13])[CH:11]=1)[O:8][C:7]([CH3:16])([CH3:15])[CH2:6][C:5]2([CH3:18])[CH3:17].C(N(CC)CC)C.Cl[C:27]1C=C(Cl)C=[C:32](Cl)[C:28]=1[C:29](Cl)=O.CC(O)(C)C>O1CCCC1.C1C=CC=CC=1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CCCCCC>[C:28]([O:13][C:12]([C:10]1[CH:11]=[C:2]([Br:1])[CH:3]=[C:4]2[C:9]=1[O:8][C:7]([CH3:16])([CH3:15])[CH2:6][C:5]2([CH3:18])[CH3:17])=[O:14])([CH3:32])([CH3:29])[CH3:27]

Participants

10

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 21107216HCID 21107216, compound2×

Product 1

HCID 57424231HCID 57424231, compoundYield 40%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 6-bromo-2,2,4,4-tetramethylchroman-8-carboxylic acid (Intermediate 41, 0.3 g, 0.96 mmol) and triethyl amine (0.1 g, 0.96 mmol) in anhydrous tetrahydrofuran (3 mL) was treated with 2,4,6-trichlorobenzoyl chloride (0.23 g, 0.96 mmol) and the reaction mixture was allowed to stir for 20 minutes. The precipitated solid was filtered off and the filtrate was evaporated in vacuo to afford a residue that was dissolved in benzene (3 mL) under argon and treated with 4-(dimethylamino)pyridine (0.47 g, 3.84 mmol) and 2-methyl-2-propanol (0.14 g, 1.92 mmol). After 18 h, the reaction mixture was diluted with ethyl acetate and washed with 2N hydrochloric acid, 2N sodium hydroxide and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title product as a white solid (0.14 g, 40%).

Workup

  1. filtrationThe precipitated solid was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customto afford a residue that
  4. waitAfter 18 h
  5. washwashed with 2N hydrochloric acid, 2N sodium hydroxide and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto afford a residue that

Sources & evidence

ORD record
ord-903660a2572f4e209a2cd5d5bba07df7
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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