Methanol → HCID 10970995, compound

HRID 2428052Notes

Reaction equation

HRID 2428052 reaction equation
[BH4-].[Li+].C([C@@H]1COC(=O)N1[C:16](=[O:41])[C@H:17]([CH3:40])[C@@H:18]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)C1C=CC=CC=1.CO>C1COCC1>[Si:33]([O:32][C@@H:18]([CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[C@@H:17]([CH3:40])[CH2:16][OH:41])([C:36]([CH3:38])([CH3:39])[CH3:37])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 10973703HCID 10973703, compound

Product 1

HCID 10970995HCID 10970995, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium borohydride (2.0 M in THF, 5 mL, 10 mmol) was added dropwise to a stirred solution of 11 (2.77 g, 5 mmol) and methanol (0.4 mL, 10 mmol) in anhydrous THF (20 mL) under an atmosphere of N2 at 0° C. The mixture was stirred for 20 min at 0° C. and then warmed to ambient temperature. After 3 h at room temperature, the reaction was quenched with aqueous NH4Cl (100 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over anhydrous MgSO4, evaporated and chromatographed (hexane/EtOAc 7:3) to yield the alcohol (1.48 g, 78%) as a colorless oil: IR (CHCl3) 2948, 2856, 2302, 1612, 1265 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.27 (d, 2H, J=8.5 Hz), 7.00 (d, 2H, J=8.5 Hz), 4.43 (s, 2H), 3.78 (s, 3H), 3.67 (dd, 1H, J=8.6, 10.5 Hz), 3.51-3.41 (m, 3H), 2.78 (br s, 1H), 1.94 (m, 1H), 1.72-1.49 (m, 4H), 0.90 (s, 9H), 0.81 (d, 3H, J=7.0 Hz), 0.09 (s, 3H), 0.08 (s, 3H); 13C NMR (75 MHz, CDCl3) 159.2, 130.6, 129.3, 113.8, 75.4, 72.6, 70.1, 65.8, 55.9, 55.3, 39.7, 29.1, 26.6, 25.9, 18.0, 12.1, −4.28, −4.38; LRMS (ESI) 405.2 (M+Na).

Workup

  1. temperaturewarmed to ambient temperature
  2. waitAfter 3 h at room temperature
  3. customthe reaction was quenched with aqueous NH4Cl (100 mL)
  4. extractionextracted with CH2Cl2 (3×20 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. customevaporated
  7. customchromatographed (hexane/EtOAc 7:3)

Sources & evidence

ORD record
ord-c931b8ca85d84a83a27b61ac69d3cfcd
Source dataset
uspto-grants-2011_06
Patent number
US07968736B2

Reaction notes

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