Sodium Thiosulfate → HCID 11736972, compound

HRID 2253426Notes

Reaction equation

HRID 2253426 reaction equation
[CH3:1][CH:2]([Si:4]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[O:5]/[C:6](/C)=[CH:7]/[CH2:8]O)[CH3:3].[CH3:17][C:18](OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:19].C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl.CCOCC>[CH3:16][CH:14]([Si:4]([CH:2]([CH3:1])[CH3:3])([CH:11]([CH3:12])[CH3:13])[O:5][CH2:6]/[C:7](/[CH3:8])=[CH:17]/[CH:18]=[O:19])[CH3:15]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86606707HCID 86606707, compound

Product 1

HCID 11736972HCID 11736972, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of (E)-3-[tris-(1-methylethyl)silyloxy]but-2-en-1-ol (crude from the previous step, assumed 17.6 mmol) in dichloromethane (100 mL) was added Dess-Martin periodinane (9.7 g, 22.9 mmol). The resulting suspension was stirred for 60 minutes, until the reaction was judged to be complete by TLC. The reaction mixture was diluted with Et2O and a saturated aqueous solution of NaHCO3 containing Na2S2O3 was added. This mixture was stirred vigorously until both layers became clear. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (5% Et2O/pentane) to afford the title compound as a colorless oil (3.69 g, 82% yield). IR (film) 2944, 2867, 1681, 1464, 1384, 1123 cm−1; 1H NMR (300 MHz, CDCl3) δ 10.09 (d, 1H, J=8.3 Hz, CHO), 6.28 (dd, 1H, J=1.5, 8.4 Hz, CH), 4.28 (d, 2H, J=0.9 Hz, CH2OTIPS), 2.09 (d, 3H, J=0.6 Hz, CH3C), 1.1 to 1.0 (m, 21H, TIPSO); 13C NMR 75 MHz, CDCl3) δ 191.2, 161.6, 124.1, 67.0, 18.0, 14.1, 11.9; HRMS (EI+) exact mass calculated for [M]+(C14H28O2Si) requires m/z 256.1859, found m/z 256.1862.

Workup

  1. customTo a room temperature
  2. additionwas added
  3. stirringThis mixture was stirred vigorously until both layers
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (5% Et2O/pentane)

Sources & evidence

ORD record
ord-9f74dfe45efc417891de8895282caeb7
Source dataset
uspto-grants-2008_01
Patent number
US07323604B2

Reaction notes

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