Bromotrimethylsilane → HCID 69929073, compound

HRID 1884321Notes

Reaction equation

HRID 1884321 reaction equation
[CH2:1]([O:4][C:5](=[O:27])[CH2:6][CH2:7][C:8]1[C:17]([CH3:18])=[C:16]2[C:11]([C:12]([CH3:21])([CH3:20])[CH2:13][C:14](=[O:19])[O:15]2)=[C:10]([CH3:22])[C:9]=1[O:23]COC)[CH:2]=[CH2:3].Br[Si](C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:4][C:5](=[O:27])[CH2:6][CH2:7][C:8]1[C:17]([CH3:18])=[C:16]2[C:11]([C:12]([CH3:20])([CH3:21])[CH2:13][C:14](=[O:19])[O:15]2)=[C:10]([CH3:22])[C:9]=1[OH:23])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 69929756HCID 69929756, compound

Product 1

HCID 69929073HCID 69929073, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-35 °C

Procedure

The compound G (393 mg, 1.04 mmol) was dissolved in 10 mL of methylene chloride and cooled to −35° C. Bromotrimethylsilane (414 μL, 3.13 mmol) was added dropwise, and the solution was stirred for 1 h. A solution of saturated NaHCO3 (15 mL) was added followed by extraction with methylene chloride (2×30 mL). The organic layers were combined and dried with MgSO4. After filtration and evaporation, the residue was purified using column chromatography with hexanes/ethyl acetate (4:1, v/v) to give 262 mg (76%) of the compound H as a white oily solid. 1H NMR 400 MHz (CDCl3) δ7.80 (s, 1H), 5.87 (m, 1H), 5.25 (m, 2H), 4.58 (d, J=5.6 Hz, 2H ), 2.92 (t, J=5.5 Hz, 2H), 2.72 (t, J=5.6 Hz, 2H), 2.50 (s, 2H), 2.36 (s, 3H), 2.19 (s, 3H), 1.43 (s, 6H).

Workup

  1. extractionfollowed by extraction with methylene chloride (2×30 mL)
  2. dry with materialdried with MgSO4
  3. filtrationAfter filtration and evaporation
  4. customthe residue was purified

Sources & evidence

ORD record
ord-5ccb9ee8bcb8464ca86bdeab488d22c0
Source dataset
uspto-grants-2004_07
Patent number
US06764768B2

Reaction notes

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