Tetrabutylammonium Fluoride → HCID 66959677, compound

HRID 1367741Notes

Reaction equation

HRID 1367741 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][CH:10]1[C:26]2([CH3:27])[CH:13]([CH:14]3[CH:23]([CH2:24][CH2:25]2)[C:22]2[CH:21]=[C:20]([O:28][CH3:29])[C:19]([OH:30])=[CH:18][C:17]=2[CH2:16][CH2:15]3)[CH2:12][CH2:11]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][CH2:7][CH2:8][O:9][CH:10]1[C:26]2([CH3:27])[CH:13]([CH:14]3[CH:23]([CH2:24][CH2:25]2)[C:22]2[CH:21]=[C:20]([O:28][CH3:29])[C:19]([OH:30])=[CH:18][C:17]=2[CH2:16][CH2:15]3)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66960256HCID 66960256, compound

Product 1

HCID 66959677HCID 66959677, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of TBS protected alcohol 47 (110 mg, 0.24 mmol) in THF (5 mL) was treated with TBAF (250 mL, 0.25 mmol). After stirring overnight the reaction was extracted with ethyl acetate (25 mL), the organics washed with water and brine, dried and evaporated. The resultant pale yellow oil was purified by column chromatography (2% methanol in chloroform) to give the desired diol 48 as a clear colourless oil (65 mg) which showed δH 6.78 (1H, s, ArH), 6.64 (1H, s, ArH), 5.51 (1H, s, OH), 3.86 (3H, s, OMe), 3.40-3.68 (5H, m, 2×OCH2 and CHOR), 2.72-2.82 (2H, m, 6-CH2), 1.20-2.30 (14H, m) and 0.81 (3H, s, 18-Me); δC 144.6, 143.5, 131.7, 129.5, 114.6, 109.1, 89.4, 70.9, 62.1, 56.1, 50.2, 44.2, 38.6, 38.0, 28.9, 28.1, 27.2, 26.6, 23.0 and 11.7.

Workup

  1. extractionwas extracted with ethyl acetate (25 mL)
  2. washthe organics washed with water and brine
  3. customdried
  4. customevaporated
  5. customThe resultant pale yellow oil was purified by column chromatography (2% methanol in chloroform)

Sources & evidence

ORD record
ord-278bb95c6175440fa6a4e8d5644c3bbb
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

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