Hydrochloric Acid → HCID 68936252, compound

HRID 388755Notes

Reaction equation

HRID 388755 reaction equation
[Si:1]([O:18][C@H:19]1[C:24](=[CH2:25])[C@H:23]([O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:22][CH:21]([O:44][Si](C(C)(C)C)(C)C)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>C(O)C>[Si:1]([O:18][C@H:19]1[C:24](=[CH2:25])[C@H:23]([O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:22][CH:21]([OH:44])[CH2:20]1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68937271HCID 68937271, compound

Product 1

HCID 68936252HCID 68936252, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of Example 19G (1.05 g, 1.43 mmol)) in ethanol (8 mL) was added concentrated HCl (104 μL, 1.28 mmol) in ethanol (2 mL), and the reaction mixture was stirred at room temperature for 3 hours. The reaction was poured into 1M NaHCO3 (35 mL) and extracted with tert-butyl methyl ether ( 3×35 mL). The combined organics were washed with brine (35 mL), dried over Na2SO4 and concentrated in vacuo to an oil. The crude material was purified by silica gel chromatography (5% ethyl acetate/hexane) then dried in vacuo at room temperature for one week to afford the titled compound (0.74 g, 83%) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 1.01 (s, 9 H) 1.02 (s, 9 H) 1.60-1.85 (m, 4 H) 2.46 (s, 1 H) 3.96-4.06 (m, 1 H) 4.63 (dd, J=6.79, 4.05 Hz, 1 H) 4.74 (t, J=5.35 Hz, 1 H) 4.85 (s, 1 H) 4.91 (s, 1 H) 7.27-7.45 (m, 12 H) 7.56-7.67 (m, 8 H); 13C NMR (100 MHz, CDCl3) δ 19.5, 19.6, 27.2, 27.3, 44.6, 67.0, 70.4, 107.9, 127.21, 127.24, 127.3, 129.33, 129.35, 129.5, 132.6, 133.2, 133.4, 133.9, 135.44, 135.48, 135.54, 135.6, 149.9; HRMS (ESI) [MNa+] calcd for C39H48O3Si2 643.3034, found 643.3022; Anal. calcd for C39H48O3Si2: C 75.43, H 7.79. Found: C 75.50, H 7.97.

Workup

  1. extractionextracted with tert-butyl methyl ether ( 3×35 mL)
  2. washThe combined organics were washed with brine (35 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo to an oil
  5. customThe crude material was purified by silica gel chromatography (5% ethyl acetate/hexane)
  6. customthen dried in vacuo at room temperature for one week

Sources & evidence

ORD record
ord-4415b96254b24b2885f22d4937f436c0
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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