Sodium hydride → HCID 57890125, compound

HRID 1819936Notes

Reaction equation

HRID 1819936 reaction equation
[C:1]([Si:5]([CH3:35])([CH3:34])[O:6][CH:7]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[S:25][C:24]([CH2:26][OH:27])=[C:23]([CH3:28])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:29])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:39][C:40]([O:42][CH3:43])=[O:41]>C1COCC1>[CH3:43][O:42][C:40](=[O:41])[CH2:39][O:27][CH2:26][C:24]1[S:25][C:21]([C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:35])[CH3:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:11]([CH3:29])[CH:12]=2)([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:22][C:23]=1[CH3:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 57890054HCID 57890054, compound

Product 1

HCID 57890125HCID 57890125, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

T a 0° C. solution of 5-(1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophen-2-yl-methanol (0.96 g, 1.85 mmol) in THF (10 mL) is added 60% NaH (81 mg, 2.0 mmol) and stirred for 20 m. The mixture is added methyl bromoacetate (0.21 mL, 2.22 mmol)warmed to RT, and stirred overnight. The reaction is quenched with satd NH4Cl (10 mL), diluted with H2O (10 mL), and extracted with EtOAc (2×20 mL). The combined organic layers is MgSO4 dried and concentrated. The resulting residue is chromatographed to give the title compound (0.33 g, 0.57 mmol, 31%). 1H NMR (CDC3), δ 0.06 (s, 3H), 0.12 (s, 3H), 0.70 (t, J=7.3 Hz, 6H), 0.91 (s, 9H), 0.97 (s, 9H), 2.01-2.10 (m, 4H), 2.19 (s, 3H), 2.20 (s, 3H), 3.67 (dd, J=5.8, 3.4 Hz, I H), 3.76 (s, 3H), 3.85 (dd, J=9.8, 5.8 Hz, 1H), 3.98 (dd, J=9.8, 3.4 Hz, 1H), 4.09 (s, 2H), 4.64 (s, 2H), 6.53 (s, 1H), 6.67 (d, J=8.3 Hz, I H), 7.00-7.06 (m, 2H). LC/MS (m/z): calcd for C 10 33H58NO5SSi (M+NH4)+: 608.9; found: 608.3.

Workup

  1. stirringstirred overnight
  2. customThe reaction is quenched with satd NH4Cl (10 mL)
  3. additiondiluted with H2O (10 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue is chromatographed

Sources & evidence

ORD record
ord-def5b644af2e468898801f706ef0700b
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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