Hydrogen Peroxide → Methyl-4'-(cis-9-octadecenyloxy)-4-biphenylcarboxylate

HRID 369528

Reaction equation

HRID 369528 reaction equation
CCOC(/N=N/C(O[CH2:11][CH3:12])=O)=O.[CH3:13][O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)=[O:16].OO.CCO[CH2:35][CH3:36].[CH2:37]1[CH2:41]O[CH2:39][CH2:38]1>>[CH3:13][O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:39][CH2:38][CH2:37][CH2:41][CH2:21][CH2:22][CH2:17][CH2:18]/[CH:19]=[CH:20]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:35][CH2:36][CH2:11][CH3:12])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)=[O:16]

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 70012153Methyl-4'-(cis-9-octadecenyloxy)-4-biphenylcarboxylateYield 41%

Conditions

Temperature
25 °C

Procedure

DEAD (676 mg, 3.88 mmol) was added via syringe with stirring and under argon, to a solution of ester 27 (590 mg, 2.59 mmol), alcohol 26b (707 mg, 2.64 mmol), and TPP (1.018 g, 3.88 mmol) in 8 ml dry THF. The reaction mixture was stirred overnight under argon at 25° C. and then treated with 30% hydrogen peroxide. Ether was added (approximately 20 ml) and the organic layer was separated, washed with brine, and dried over MgSO4. The crude product was adsorbed onto silica gel and purified via flash chromatography with elutions of 95/5 and 90/10 (v/v) (Hex/EtOAc), respectively. Evaporation of solvent yielded 505 mg (41%) of a white solid.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. custompurified via flash chromatography with elutions of 95/5 and 90/10 (v/v) (Hex/EtOAc)
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-c1454863aaa84ffca2f2ba3859a215ce
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Linked notes

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