Methanol → HCID 11381060, compound

HRID 646812Notes

Reaction equation

HRID 646812 reaction equation
OC[C:3]([CH3:19])(C)[CH2:4][CH2:5][CH2:6][C:7](=[O:17])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14].[O:20]1[CH2:25][CH2:24][CH2:23]CC1.[H-].[Na+].[CH3:28]O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.Cl>[OH:14][CH2:13][C:12]([CH3:15])([CH3:16])[CH2:11][CH2:10][CH2:9][CH2:8][C:7](=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:19][C:24]([CH3:28])([CH3:23])[CH2:25][OH:20]

Participants

8

Reactant 4

HCID 887MethanolHCID 8894TetrahydropyranHCID 24758Sodium hydrideHCID 11208035HCID 11208035, compound

Product 1

HCID 11381060HCID 11381060, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

According to the procedure described for the synthesis of 217, 215 (6.98 g, 17.1 mmol) was reacted with NaH (0.82 g, 20.5 mmol, 60% in mineral oil), 207g (5.8 g, 18.9 mmol), and tetrabutylammonium iodide (0.63 g, 1.7 mmol) in anhydrous DMSO (100 mL) for 24 h at room temperature. The crude intermediate (10.9 g) obtained after aqueous workup was heated to reflux in concentrated HCl (18 mL) and methanol (100 mL) overnight. After extraction and column chromatography (silica gel; hexanes/ethyl acetate=80/20), 219 (2.3 g, 48%) was obtained as a colorless oil. 1H NMR (CDCl3): δ 3.30 (s, 4H), 2.48-2.34 (m, 4H), 1.85 (br., 2H), 1.66-1.46 (m, 4H), 1.24-1.14 (m, 10H), 0.85 (s, 12H). 13C NMR (CDCl3): δ 211.8, 71.8, 71.6, 42.7, 42.6, 38.4, 38.2, 34.9, 30.1, 24.6, 23.8, 23.8, 23.7, 23.6, 23.4. HRMS (LSIMS, gly): Calcd for C18H37O3 (MH+): 301.2743, found: 301.2745. HPLC: 97.4% pure.

Workup

  1. customThe crude intermediate (10.9 g) obtained after aqueous workup
  2. temperaturewas heated
  3. extractionAfter extraction and column chromatography (silica gel; hexanes/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-87d1454d82194b248348bb6cf7683706
Source dataset
uspto-grants-2010_04
Patent number
US07705177B2

Reaction notes

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