Phenol → HCID 53781463, compound

HRID 327859Notes

Reaction equation

HRID 327859 reaction equation
[Si:1]([O:8][C@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][C:11]([OH:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:25]1(O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Si:1]([O:8][C@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:10][C:11]([O:13][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 54310188(R)-3-[(1,1-dimethylethyl)dimethylsilyloxy]tetradecanoic acid

Product 1

HCID 53781463HCID 53781463, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 2.71 g (R)-3-t-butyldimethylsilyloxytetradecanoic acid (0.0076 moles) in 20 mL dichloromethane was cooled with stirring to 5° C. 0.72 g Phenol (0.0076 moles), then 1.72 g N,N'-dicyclohexylcarbodiimide (0.0084 moles) were added and the resultant mixture was allowed to warm to room temperature and stirred there for about 16 hours. The mixture was filtered through a coarse sintered glass funnel, and the collected solids were washed with about 5 mL dichloromethane. The combined filtrate and washes were concentrated to dryness on a rotary evaporator (about 100 mm Hg, 30° C.). The residue was chromatographed on a 2" column slurry packed with silica gel (about 150 g) in dichloro- methane. The product was eluted with dichloromethane. The chromatography was monitored by TLC (silica gel, dichloromethane, phosphomolybdic acid visualization, product Rf ca 0.95). Fractions containing only product were pooled and concentrated to an oil on a rotary evaporator (ca. 125 mm Hg, 30° C.). The oil was blown dry by passing a stream of nitrogen over it for 1 hour. A clear oil (2.71 g, 82% yield) was obtained.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred there for about 16 hours
  3. filtrationThe mixture was filtered through a coarse sintered glass funnel
  4. washthe collected solids were washed with about 5 mL dichloromethane
  5. concentrationThe combined filtrate and washes were concentrated to dryness on a rotary evaporator (about 100 mm Hg, 30° C.)
  6. customThe residue was chromatographed on a 2" column slurry
  7. washThe product was eluted with dichloromethane
  8. additionFractions containing only product
  9. concentrationconcentrated to an oil on a rotary evaporator (ca. 125 mm Hg, 30° C.)
  10. customThe oil was blown dry
  11. customfor 1 hour

Sources & evidence

ORD record
ord-164d803f5b1f4ed0a4e23880646a19c5
Source dataset
uspto-grants-1993_12
Patent number
US05274143

Reaction notes

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