HCID 52919353, compound → HCID 58250163, compound

HRID 1045080Notes

Reaction equation

HRID 1045080 reaction equation
[C:1]([Si:5]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])([CH3:4])([CH3:3])[CH3:2].[Li][CH2:41][CH2:42][CH2:43][CH3:44]>C1COCC1>[C:1]([Si:5]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:44][CH2:43][CH2:42][CH2:41]/[CH:41]=[CH:42]\[CH2:43]/[CH:44]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 52919353HCID 52919353, compoundHCID 178418339Butyllithium

Product 1

HCID 58250163HCID 58250163, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyldiphenyl(12-(phenylsulfonyl)dodecyloxy)silane (0.381 g, 0.675 mmol) in THF (2 mL) was added n-BuLi (2.5 M solution in hexanes, 0.297 mL, 0.742 mmol) at −78° C. under Argon. After stirring the resulting solution for 30 min, the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction mixture was quenched with saturated aqueous NH4Cl (2 mL) at −10° C. and the aqueous phase was extracted with DCM (3×15 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude was purified by silica gel column chromatography using 5% ethyl acetate/hexane to afford the title product as a clear thick oil (0.16 g, 85%). 1H NMR (CDCl3): δ7.89-7.39 (m, 15H), 5.37 (m, 8H), 3.64 (t, 2H, J=6.5 Hz), 2.78 (m, 7H), 2.08 (m, 4H), 1.82 (m, 2H), 1.37-1.20 (m, 30H), 1.04 (s, 9H), 1.04 (t, 3H, J=6.7 Hz). m/z (ESI) 837.74 (M++1).

Workup

  1. stirringstirred overnight
  2. customThe reaction mixture was quenched with saturated aqueous NH4Cl (2 mL) at −10° C.
  3. extractionthe aqueous phase was extracted with DCM (3×15 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-04c6f3bc58d64ffca0208ecbf7115791
Source dataset
uspto-grants-2013_10
Patent number
US08563760B2

Reaction notes

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