Tetrahydrofuran → HCID 19902684, compound

HRID 2373089Notes

Reaction equation

HRID 2373089 reaction equation
C([O:8][CH2:9][C:10]1([Si:31]([CH3:34])([CH3:33])[CH3:32])[C:22]2[CH:21]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][C:13]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:14][CH:15]=2)C1C=CC=CC=1.C1COCC1>[Pd].CCO>[C:23]([C:20]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([C:27]([CH3:29])([CH3:30])[CH3:28])=[CH:14][CH:15]=3)[C:10]([Si:31]([CH3:34])([CH3:33])[CH3:32])([CH2:9][OH:8])[C:22]=2[CH:21]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 19902697HCID 19902697, compound

Product 1

HCID 19902684HCID 19902684, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4.0 g of 2,7-di-tert-butyl-9-trimethylsilyl-9-fluorenylmethyl benzyl ether in 20 mL of freshly distilled THF and 80 mL of 100% EtOH was added 0.8 g of 5% palladium on charcoal. The heterogeneous mixture was shaken under hydrogen at a pressure of 45 psi in a Parr apparatus for 2 hours. The catalyst was removed by filtration and rinsed with ether (2×10 mL). The filtrate was evaporated under reduced pressure to give 3.23 g (100%) of the crude alcohol as a yellow oil which was chromatographed on silica gel (230-400 mesh, 4×45-cm packed column) with an eluant consisting of Skelly B--ether (3:1), to give 3.12 g (96.4%) of the alcohol as a white solid. Recrystallization from Skelly B gave 2.57 g (79.44%) of the pure alcohol as white needles, m.p. 131°-132° C.; IR (KBr): 3545, 3495 cm-1 (OH); 1H NMR (CDCl3): δ -0.18 (s, 9H, SiMe3), 1.20 (b, 1H, OH), 1.39 (s, 18H, t-Bu), 4.50 (s, 2H, CH2), 7.20-7.90 (m, 6H, aryl).

Workup

  1. customThe catalyst was removed by filtration
  2. washrinsed with ether (2×10 mL)
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b141a6e3e1fc44969cce5337e7f05419
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

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