Monobenzone → HCID 66930919, compound

HRID 511995Notes

Reaction equation

HRID 511995 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].[CH2:19]([O:26]C1C=CC(O)=CC=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+].BrCCCCCCC(OCC)=O>CC(C)=O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:17]=1)[CH3:2]

Participants

7

Reactant 5

HCID 7638MonobenzoneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 122490Ethyl 7-bromoheptanoateHCID 66930916HCID 66930916, compound

Product 1

HCID 66930919HCID 66930919, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An alternative method for the synthesis of the title compound was carried out analogous to the preparation of 61.1 using 60.2 (0.45 g, 2.255 mmol), 18-crown-6 (1.056 g, 4 mmol), potassium carbonate (1.38 g, 10 mmol), and Br(CH2)6COOEt, (0.8 g, 3.37 mmol) in dry acetone (40 mL). Purification by flash column chromatography on silica gel (20% diethyl ether-hexane) gave 61.2/20.4 (1.08 g, 90% yield) as a white solid (m p 57-61° C.).

Workup

  1. customPurification by flash column chromatography on silica gel (20% diethyl ether-hexane)

Sources & evidence

ORD record
ord-0e7cfa61c5874df3b1d0784d6c47425d
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

Loading…