Hexane → HCID 18431832, compound

HRID 2188360Notes

Reaction equation

C([O:9][CH:10]1[CH2:17][CH:16]2[CH:12]([CH2:13][C:14](=[O:18])[O:15]2)[CH:11]1[CH:19]1[O:23][CH2:22][CH2:21][O:20]1)(=O)C1C=CC=CC=1.C[O-].[Na+].CCCCCC.C(OCC)(=O)C>CO.C(Cl)Cl>[CH:19]1([CH:11]2[CH:10]([OH:9])[CH2:17][CH:16]3[CH:12]2[CH2:13][C:14](=[O:18])[O:15]3)[O:23][CH2:22][CH2:21][O:20]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a well stirred solution of crude 1b (63.85 g, 201 mmol, 1 eq) in methanol (786 mL) at 0° C. is added a suspension of sodium methoxide (13.27 g, 246 mmol, 1.2 eq) in MeOH (98.3 mL). The reaction is stirred at 0° C. for 1 hour and then is warmed to 25° C. for 1 hour. The reaction is neutralized with acidic ion exchange resin which has been washed thoroughly with MeOH (5×100 mL). The filtrate is concentrated in vacuo to give a syrup which is subjected to flash chromatography on silica gel eluting with 4:1 hexane:ethyl acetate and 2% MeOH in CH2Cl2 to give 1c as a yellow syrup.

Workup

temperatureis warmed to 25° C. for 1 hour
washhas been washed thoroughly with MeOH (5×100 mL)
concentrationThe filtrate is concentrated in vacuo
customto give a syrup which

Sources & evidence

ORD record: ord-e8d49e0bfb6c4bce8c9e6c6f3a9137db
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410780B1

Reaction notes

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