Ethanol → HCID 12133739, compound

HRID 352699Notes

Reaction equation

HRID 352699 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]=2[C:18]([CH3:29])([CH3:28])[CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[CH2:30](O)[CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]=2[C:18]([CH3:29])([CH3:28])[CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:30][CH3:31])=[O:26])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12133737HCID 12133737, compound2×

Product 1

HCID 12133739HCID 12133739, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a nitrogen atmosphere at room temperature, to a THF (2.5 mL) solution having 5-(3-acetoxyphenyl)-4-(7-carboxy-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran (compound (15)) (209 mg, 0.5167 mmol) dissolved, ethanol (48 mg, 1.042 mmol, 2.0 eq.) and triphenyl phosphine (275 mg, 1.048 mmol, 2.0 eq.) were added, and further diethyl azodicarboxylate (185 mg, 1.062 mmol, 2.1 eq.) dissolved in THF (0.5 mL) was added, followed by stirring for 20 minutes. This reaction solution was put into a 1N hydrochloric aqueous solution and a saturated sodium chloride aqueous solution, and extracted with ethyl acetate. The aqueous layer was again extracted with ethyl acetate, and the extract was put together with the previous organic layer, followed by washing with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain a residue. This residue was subjected to silica gel column chromatography with a developing solvent (ethyl acetate:hexane=1:20). As a result, the desired 5-(3-acetoxyphenyl)-4-(7-ethoxycarbonyl-1,1-dimethyl-3-oxaheptyl)-3,3-dimethyl-2,3-dihydrofuran (compound (17)) was obtained as a colorless oil (172 mg, 0.3976 mmol, 77.0%).

Workup

  1. customat room temperature
  2. dissolutiondissolved
  3. additionwas added
  4. extractiona saturated sodium chloride aqueous solution, and extracted with ethyl acetate
  5. extractionThe aqueous layer was again extracted with ethyl acetate
  6. washby washing with a saturated sodium hydrogencarbonate aqueous solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto obtain a residue

Sources & evidence

ORD record
ord-1df13afd20dc4f68bace2f3513793fa2
Source dataset
uspto-grants-2004_06
Patent number
US06747160B2

Reaction notes

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