Borane → HCID 58593384, compound

HRID 917000Notes

Reaction equation

HRID 917000 reaction equation
[C:1]([C:5]1[CH:15]=[C:14]([S:16][C:17]([S:20][C:21]2[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24]([OH:31])=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:22]=2)([CH3:19])[CH3:18])[CH:13]=[C:12]([C:36]([CH3:39])([CH3:38])[CH3:37])[C:6]=1[O:7][CH2:8][C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:32]([C:23]1[CH:22]=[C:21]([S:20][C:17]([S:16][C:14]2[CH:13]=[C:12]([C:36]([CH3:37])([CH3:38])[CH3:39])[C:6]([O:7][CH2:8][CH2:9][OH:10])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:15]=2)([CH3:19])[CH3:18])[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24]=1[OH:31])([CH3:33])([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 6331BoraneHCID 9875498Camobucol

Product 1

HCID 58593384HCID 58593384, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 100 mL, 2-neck round bottom flask equipped with a nitrogen adapter and a temperature probe was charged with 5.0 g (8.7 mmol, 1 eq) of {2,6-Di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenoxy}-acetic acid and 40 mL of anhydrous THF. The solution was cooled to 0° C. using an ice bath and 26.1 mL of 1.0 M (26.1 mmol, 3 eq) borane in THF at a rate such that the maximum temperature was less than 30° C. The solution was warmed to 30° C. and consumption of starting material was monitored by TLC. After 4 hours, the flask was cooled to 0° C. using an ice bath and 75 mL of methanol was slowly added. The resulting solution was concentrated under reduced pressure. The resulting oil was dissolved in 50 mL of methanol and concentrated under reduced pressure two more times. The residue was slurried in 50 mL of hexanes and concentrated under reduced pressure a total of 4 times. The residue was taken up in 50 mL of hexanes and the product was allowed to slowly precipitate. The precipitate was collected by vacuum filtration, washed with 10 mL of hexanes and dried in vacuo to yield 3.1 g (5.6 mmol, 64% yield) of the title compound as a white powder, mp 146–147° C.; 1H NMR (300 MHz, CDCl3) d 7.56 (s, 2H), 7.45 (s, 2H), 5.37 (s, 1H), 4.03 (t, J=5.2 Hz, 2H), 2H), 3.92 (t, J=5.1 Hz, 2H), 1.47 (s, 6H), 1.46 (s, 18H), 1.45 (s, 18H). Anal. calcd for C33H52O3S2: C70.66, H9.34, S11.43; found: C70.36, H9.37, S11.35. HRMS (EI+), m/z: calc. 560.3358; Found 560.3347

Workup

  1. customA 100 mL, 2-neck round bottom flask equipped with a nitrogen adapter
  2. customwas less than 30° C
  3. temperatureThe solution was warmed to 30° C.
  4. customconsumption of starting material
  5. temperaturethe flask was cooled to 0° C.
  6. addition75 mL of methanol was slowly added
  7. concentrationThe resulting solution was concentrated under reduced pressure
  8. dissolutionThe resulting oil was dissolved in 50 mL of methanol
  9. concentrationconcentrated under reduced pressure two more times
  10. concentrationconcentrated under reduced pressure a total of 4 times
  11. customto slowly precipitate
  12. filtrationThe precipitate was collected by vacuum filtration
  13. washwashed with 10 mL of hexanes
  14. customdried in vacuo

Sources & evidence

ORD record
ord-8ce4012a90af42bcaf14183c2c3b2aea
Source dataset
uspto-grants-2007_09
Patent number
US07271274B2

Reaction notes

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