Water → HCID 10325372, compound

HRID 1784164Notes

Reaction equation

HRID 1784164 reaction equation
[C:1]1([S:7]([C:10]2[C@@H:11]([OH:35])[C@@H:12]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C@H:13]([CH3:26])[C@H:14]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@@H:15]([CH3:17])[CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:36]I.[OH-].[K+].O>CS(C)=O.C(OCC)(=O)C.CCCCCC>[C:1]1([S:7]([C:10]2[C@@H:11]([O:35][CH3:36])[C@@H:12]([O:27][Si:28]([C:31]([CH3:33])([CH3:32])[CH3:34])([CH3:29])[CH3:30])[C@H:13]([CH3:26])[C@H:14]([O:18][Si:19]([C:22]([CH3:24])([CH3:25])[CH3:23])([CH3:21])[CH3:20])[C@@H:15]([CH3:17])[CH:16]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 10256786HCID 10256786, compound

Product 1

HCID 10325372HCID 10325372, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of compound 52 (75 mg, 0.14 mmol) and MeI (86 μL, 1.4 mmol) in DMSO (2.0 mL) was added powdered KOH (23 mg, 0.42 mmol) and the resulting mixture was stirred for 5 min (until no starting material was present by TLC, developed in 1:3 EA/hexanes) at room temperature. 5 mL of H2O was added, and extracted with diethyl ether (3×5 mL). The organic layers were combined washed with brine, dried over anhydrous Na2SO4 and concentrated. Flash chromatography (ethyl acetate/hexane, 1:10) afforded 72 mg (yield 94%) of compound 53 as a colorless oil which slowly solidified when left standing. m.p.=94.0° C.-96.0° C.; [α]20D=−39.7 (c=0.65, CHCl3); 1H NMR (CDCl3, 300 MHz) δ 7.86-7.89 (m, 2H), 7.51-7.61 (m, 3H), 7.35 (d, J=7.8 Hz, 1H), 3.98 (s, 1H), 3.83 (d, J=3.9 Hz, 1H), 3.57 (d, J=9.3 Hz, 1H), 3.35 (s, 3H), 2.77 (m, 1H), 2.54 (m, 1H), 1.23 (d, J=7.2 Hz, 3H), 1.01 (d, J=7.2 Hz, 3H), 0.91 (s, 9H), 0.84 (s, 9H), 0.09 (s, 3H), 0.07 (s, 3H), −0.14 (s, 3H), −0.31 (s, 3H). 13C NMR (CDCl3, 75 MHz) δ 149.4, 140.3, 139.9, 133.4, 129.4, 128.3, 79.8, 78.7, 73.7, 59.4, 40.2, 36.6, 26.1, 28.3, 18.2, 17.7, 16.9, −4.1, −4.5, −4.6, −4.7; LRMS (CI) m/z 555 [M+H]+; HRMS (CI) calculated for C28H50O5SSi2, 555.2996; found, 555.2998.

Workup

  1. customat room temperature
  2. extractionextracted with diethyl ether (3×5 mL)
  3. washThe organic layers were combined washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b1782a0af1a84ba9b389e90c07478f26
Source dataset
uspto-grants-2009_03
Patent number
US07501535B2

Reaction notes

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