Pyridine → HCID 86586616, compound

HRID 348236Notes

Reaction equation

HRID 348236 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].N1C=CC=CC=1.[CH:16]([O:19][CH:20]([O:35][CH:36]([CH3:38])[CH3:37])[C:21]([CH3:34])([CH3:33])[C:22](=[O:32])[C@H:23]([CH3:31])[C@@H:24]([OH:30])[C@@H:25]([CH3:29])[CH2:26][CH:27]=[CH2:28])([CH3:18])[CH3:17].[Na+].[Cl-]>C(Cl)Cl>[CH:36]([O:35][CH:20]([O:19][CH:16]([CH3:18])[CH3:17])[C:21]([CH3:33])([CH3:34])[C:22](=[O:32])[C@H:23]([CH3:31])[C@@H:24]([O:30][C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3])[C@@H:25]([CH3:29])[CH2:26][CH:27]=[CH2:28])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 870632,2,2-Trichloroethyl chloroformateHCID 11198250(4R,5S,6S)-1,1-diisopropoxy-5-hydroxy-2,2,4,6-tetramethyl-8-nonen-3-one

Product 1

HCID 86586616HCID 86586616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trichloroethyl chloroformate (2.5 mL) and pyridine (2.95 mL) are added to a solution of (4R,5S,6S)-1,1-diisopropoxy-5-hydroxy-2,2,4,6-tetramethyl-8-nonen-3-one (3.0 g) in 40 mL of CH2Cl2 at 0° C., and the mixture is stirred for 5 hours before pouring into sat. aq. NaCl and extracting with CH2Cl2. The extract is dried over Na2SO4, filtered, and evaporated. The product is purified by chromatography on SiO2 (2% ethyl acetate/hexanes).

Workup

  1. extractionextracting with CH2Cl2
  2. dry with materialThe extract is dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe product is purified by chromatography on SiO2 (2% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c67536ddff554158a34cf8d2a9600ea7
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Reaction notes

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