Methanol → HCID 11381060, compound

HRID 873280Notes

Reaction equation

HRID 873280 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].[N+](C(S(C1C=CC(C)=CC=1)(=O)=O)CCC[CH2:26][C:27](C)([CH3:36])[CH2:28][O:29]C1CCCCO1)#[C-].[H-].[Na+].CO>[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:27]([CH3:36])([CH3:26])[CH2:28][OH:29]

Participants

8

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 11208035HCID 11208035, compoundHCID 11452545HCID 11452545, 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-41e011414ef146ce867860a4dfc64207
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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