Methanol → HCID 11381060, compound

HRID 661157Notes

Reaction equation

HRID 661157 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-67d178c9a64a4e0a8933a480f1f94c39
Source dataset
uspto-grants-2011_12
Patent number
US08084498B2

Reaction notes

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