TBAF tetrahydrofuran → HCID 57890208, compound

HRID 1819937Notes

Reaction equation

HRID 1819937 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][O:5][CH2:6][C:7]1[S:8][C:9]([C:13]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([O:31][Si](C(C)(C)C)(C)C)[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:20]([CH3:39])[CH:19]=2)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:11]=1[CH3:12].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[CH2:14]([C:13]([C:9]1[S:8][C:7]([CH2:6][O:5][CH2:4][C:3]([OH:40])=[O:2])=[C:11]([CH3:12])[CH:10]=1)([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([OH:31])[C:27]([CH3:29])([CH3:30])[CH3:28])=[C:20]([CH3:39])[CH:19]=1)[CH2:16][CH3:17])[CH3:15]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 57890125HCID 57890125, compound

Product 1

HCID 57890208HCID 57890208, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[5-(1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophen-2-ylmethoxy]-acetic acid methyl ester (0.33 g, 0.57 mmol), 1.0 M TBAF/THF (0.62 m L, 0.62 mmol) and THF (4 mL) is refluxed for 3 h. The mixture filtered through silica gel, washed with EtOAc and concentrated. The resulting residue is hydrolyzed using a procedure analogous to Example 47 to give the title compound (0.13 g, 0.28 mmol) in an overall yield of 49%. 1H NMR (CDC3), δ 0.71 (t, J=7.4 Hz, 6H), 1.02 (s, 9H), 2.01-2.10 (m, 4H), 2.19 (s, 3H), 2.20 (s, 3H), 2.21 (bs, 2H), 3.72 (dd, J=8.8, 2.9 Hz, 1H), 3.87 (t, J=8.8 Hz, 1H), 4.08-4.12 (m, 2H), 4.16 (s, 1H), 4.66 (s, 1H), 5.24 (s, 1H), 6.54 (d, J=3.4 Hz, 1H), 6.62 (d, J=8.3 Hz, 1H), 7.01-7.08 (m, 2H). LC/MS (m/z): calcd for C26H37O5S (M−H)−: 461.7; found: 461.2.

Workup

  1. filtrationThe mixture filtered through silica gel
  2. washwashed with EtOAc
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8f7cacfa6e344dd9905c367f9c0caeb5
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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