Dimethyl Sulfate → HCID 14722831, compound

HRID 1613514Notes

Reaction equation

HRID 1613514 reaction equation
[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:26]=[CH:25][C:16]3[CH2:17][CH2:18][CH:19]([C:21]([O:23][CH3:24])=[O:22])[O:20][C:15]=3[C:14]=2[CH2:27][CH2:28][CH3:29])=[C:6]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:5]=1[OH:36])(=[O:3])[CH3:2].[OH-].[K+].S(OC)(O[CH3:43])(=O)=O.C(OCC)C.O>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:26]=[CH:25][C:16]3[CH2:17][CH2:18][CH:19]([C:21]([O:23][CH3:24])=[O:22])[O:20][C:15]=3[C:14]=2[CH2:27][CH2:28][CH3:29])=[C:6]([CH2:32][CH:33]2[CH2:34][CH2:35]2)[C:5]=1[O:36][CH3:43])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 14722830HCID 14722830, compoundHCID 21584184Diethylether water

Product 1

HCID 14722831HCID 14722831, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Methyl 7-[3-[4-acetyl-2-(cyclopropylmethyl)-3-hydroxyphenoxy]propoxy]-3,4-dihydro-8-propyl-2H-1-benzopyran-2-carboxylate (0.69 g, 1.39 mmol) was stirred in 15 mL THF with 0.20 g (3.57 mmol) potassium hydroxide and 0.34 mL (3.59 mmol) dimethyl sulfate at room temperature for 3.5 hr. The mixture was poured into ethyl ether/water, and the ether layer was washed with brine, dried over sodium sulfate, and concentrated. Flash chromatography on silica gel using 10:1 to 5:1 hexane/ethyl acetate as eluant provided the product (0.705 g, 1.38 mmol, 99% yield). High resolution mass spectrum, m/e 510.2612 (calculated for C30H38O7, 510.2617).

Workup

  1. washthe ether layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b5b2cdbf5c004375a814c2a0d4586ed4
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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