Water → HCID 54175553, compound

HRID 481813Notes

Reaction equation

HRID 481813 reaction equation
CC([Si](C)(C)[O:6][C:7]([C:10]#[C:11][CH2:12][C@H:13]([C:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:24]([O:42][Si](C)(C)C(C)(C)C(C)C)[CH2:25][C@@H:26]2[O:34][Si](CC)(CC)CC)=[CH:21][CH:20]=3)[CH2:17][CH:16]=1)[CH3:14])([CH3:9])[CH3:8])(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].CCOC(C)=O.O>O1CCCC1>[CH3:8][C:7]([OH:6])([C:10]#[C:11][CH2:12][C@H:13]([C:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:24]([OH:42])[CH2:25][C@@H:26]2[OH:34])=[CH:21][CH:20]=3)[CH2:17][CH:16]=1)[CH3:14])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86753001HCID 86753001, compound

Product 1

HCID 54175553HCID 54175553, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 20.7 g (26.5 mmol) of (1α,3β)-[[25-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]cholesta-5,7,16-trien-23-yn-1-yl]oxy]triethylsilane and 265 mL (265 mmol) of 1M Bu4NF in tetrahydrofuran was stirred at 30°-35° C. for 40 hr. After cooling to room temperature, 265 mL of EtOAc and 265 mL of water were added. The aqueous layer was extracted with 2×125 mL of EtOAc. The combined EtOAc solutions were concentrated to dryness. The residue was suspended in 130 mL of hexane and 130 mL of water, and the mixture was stirred for 30 min prior to filtration. The solid was washed with 130 mL of water and then with 130 mL of hexane. After being dried by suction, the solid was dissolved in 90 mL of hot methanol. After the solution was diluted with 45 mL of water and cooled to room temperature, the mixture was stored in a refrigerator overnight. The precipitate was filtered and washed with 100 mL of methanol-water (2:1). Drying at room temperature under high vacuum for 24 hr gave 9.37 g of (1α,3β)-cholesta-5,7,16-trien-23-yne-1,3,25-triol

Workup

  1. extractionThe aqueous layer was extracted with 2×125 mL of EtOAc
  2. concentrationThe combined EtOAc solutions were concentrated to dryness
  3. stirring130 mL of water, and the mixture was stirred for 30 min
  4. filtrationto filtration
  5. washThe solid was washed with 130 mL of water
  6. customAfter being dried by suction
  7. dissolutionthe solid was dissolved in 90 mL of hot methanol
  8. additionAfter the solution was diluted with 45 mL of water
  9. temperaturecooled to room temperature
  10. customwas stored in a refrigerator overnight
  11. filtrationThe precipitate was filtered
  12. washwashed with 100 mL of methanol-water (2:1)
  13. customDrying at room temperature under high vacuum for 24 hr

Sources & evidence

ORD record
ord-d636ac274d7c4566a59d3dcab98a06fb
Source dataset
uspto-grants-1998_08
Patent number
US05789607

Reaction notes

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