Hydrochloric Acid → HCID 21940186, compound

HRID 1242828Notes

Reaction equation

HRID 1242828 reaction equation
[CH2:1](O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:23]([O:26][C:27]1[CH:28]=[C:29]([C:33]2[O:37][CH2:36][C:35]([CH3:39])([CH3:38])[C:34]=2[C:40]([CH3:57])([CH3:56])[CH2:41][O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53]([OH:55])=[O:54])[CH:30]=[CH:31][CH:32]=1)(=[O:25])[CH3:24].N(C(OCC)=O)=NC(OCC)=O.Cl>C1COCC1>[C:23]([O:26][C:27]1[CH:28]=[C:29]([C:33]2[O:37][CH2:36][C:35]([CH3:39])([CH3:38])[C:34]=2[C:40]([CH3:57])([CH3:56])[CH2:41][O:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53]([O:55][CH2:1][CH3:2])=[O:54])[CH:30]=[CH:31][CH:32]=1)(=[O:25])[CH3:24]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21940188HCID 21940188, compound2×

Product 1

HCID 21940186HCID 21940186, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution having ethanol (34 mg, 0.74 mmol), triphenyl phosphine (204 mg, 0.78 mmol) and 5-(3-acetoxyphenyl)-4-(13-carboxy-1,1-dimethyl-3-oxatridecan-1-yl)-3,3-dimethyl-2,3-dihydrofuran (compound (22)) (126 mg, 0.258 mmol) dissolved in anhydrous THF (1.0 mL) in a nitrogen stream at room temperature and stirred, diethyl azodicarboxylate (135 mg, 0.77 mmol) dissolved in anhydrous THF (0.5 mL), was added, followed by stirring for 20 minutes. After completion of the reaction, the reaction mixture was put into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was put into a silica gel column and developed with a mixed solvent of hexane and ethyl acetate (20:1 to 10:1), whereby 5-(3-acetoxyphenyl)-4-(13-ethoxycarbonyl-1,1-dimethyl-3-oxatridecan-1-yl)-3,3-dimethyl-2,3-dihydrofuran (compound (24)) was obtained as a colorless oil in an amount of 111 mg in a yield of 83.3%.

Workup

  1. additionwas added
  2. stirringby stirring for 20 minutes
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5d14d799f8fd4bc8af46a4d7ec256bc1
Source dataset
uspto-grants-2006_10
Patent number
US07115757B2

Reaction notes

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