Dichloromethane methanol → HCID 11185602, compound

HRID 2118391Notes

Reaction equation

HRID 2118391 reaction equation
COC[O:4][C:5]1[CH:14]=[CH:13][C:12]2[O:11][CH:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21]COC)=[CH:17][CH:16]=3)[CH:9]3[CH2:25][CH:26]([OH:28])[CH2:27][CH:8]3[C:7]=2[CH:6]=1.CO.C(Cl)Cl>C1COCC1.Cl.CCOC(C)=O>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([C@H:10]2[C@H:9]3[CH2:25][C@@H:26]([OH:28])[CH2:27][C@H:8]3[C:7]3[CH:6]=[C:5]([OH:4])[CH:14]=[CH:13][C:12]=3[O:11]2)=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 21226129Dichloromethane methanolHCID 68706007HCID 68706007, compound

Product 1

HCID 11185602HCID 11185602, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stir a solution of alcohol 25 (60 mg, 0.16 mmol) in 2 mL of THF and 2 mL of 3 M HCl overnight. Dilute the solution with EtOAc. Separate the aqueous solution and extract 2× with 10% MeOH in EtOAc. Wash the combined organic solutions with saturated aqueous sodium bicarbonate, brine, dry over Na2SO4, filter, and concentrate. Absorb to 1 g silica gel. Purify by silica gel chromatography (4 g silica gel, 0 to 10% MeOH/CH2Cl2 then 20% MeOH/CH2Cl2) to give 37 mg, (0.12 mmol, 79%) of alcohol 26. HPLC (Zorbax C18 column 10 to 100% CH3CN/H2O for 10 min then 100% CH3CN for 5 min; 1 mL/min; tr 7.79 min). LRMS(ES−) calcd for C18H15O4: 297.11; found: 297.29 (M−H).

Workup

  1. customSeparate the aqueous solution
  2. extractionextract 2× with 10% MeOH in EtOAc
  3. washWash the combined organic solutions with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customAbsorb to 1 g silica gel
  8. customPurify by silica gel chromatography (4 g silica gel, 0 to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-6ec68ef3801047319263a8d239072161
Source dataset
uspto-grants-2008_10
Patent number
US07442812B2

Reaction notes

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