Tetrahydrofuran → HCID 9945800, compound

HRID 1263532Notes

Reaction equation

HRID 1263532 reaction equation
C([C:8](=[C:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][Si](C(C)(C)C)(C)C)=[CH:20][C:19]=2O[Si](C(C)(C)C)(C)C)[CH2:14][CH2:13]1)[C:9]([O-:11])=[O:10])C1C=CC=CC=1.O1[CH2:44][CH2:43][CH2:42][CH2:41]1.[OH2:45].[F-].[CH2:47]([N+](CCCC)(CCCC)CCCC)[CH2:48][CH2:49]C>C(O)(=O)C>[OH:45][C:23]1[CH:22]=[C:21]([OH:24])[CH:20]=[CH:19][C:18]=1[CH:15]1[CH2:14][CH2:13][C:12](=[CH:8][C:9]([O:11][CH2:41][C:42]2[CH:49]=[CH:48][CH:47]=[CH:44][CH:43]=2)=[O:10])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 86758895HCID 86758895, compound

Product 1

HCID 9945800HCID 9945800, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added benzyl[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexylidene]acetate (232 mg), tetrahydrofuran (5 ml), tetrabutylammonium fluoride hydrate (429 mg) and glacial acetic acid (94 μl). After stirring at room temperature for 0.5 hr, the solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 ml) and water (20 ml). The layers were separated and the aqueous phase was extracted with ethyl acetate (50 ml). The combined organic phases were washed with water (50 ml), brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 1:3 v/v) furnished the title compound (100 mg, 72%) as a cream solid. δH (CD3OD): 1.59-1.67 (2H, m), 1.98-2.13 (4H, m), 2.37-2.48 (2H, m), 3.14 (1 H, tt), 5.16 (2H, s), 5.75 (1 H, s), 6.26 (1 H, dd), 6.30 (1 H, d), 6.89 (1 H, d), 7.30-7.44 (5H, m); m/z (ES−) 337 (M−H)−.

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. customthe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate (100 ml) and water (20 ml)
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (50 ml)
  6. washThe combined organic phases were washed with water (50 ml), brine (20 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 1:3 v/v)

Sources & evidence

ORD record
ord-0b2534716fa9432784a49be5389df400
Source dataset
uspto-grants-2003_04
Patent number
US06541473B2

Reaction notes

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