Water → HCID 86594473, compound

HRID 1744217Notes

Reaction equation

HRID 1744217 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:9]2([CH3:10])[C@@H:8]([OH:26])[CH2:7]1)[C:20]1[CH:19]=[CH:18][C:17]([O:24][CH3:25])=[CH:16][C:15]=1[CH2:14][CH2:13]3)=[O:5])[CH3:2].[CH2:27](Cl)[O:28][CH3:29].O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C@@H:6]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:9]2([CH3:10])[C@@H:8]([O:26][CH2:27][O:28][CH3:29])[CH2:7]1)[C:20]1[CH:19]=[CH:18][C:17]([O:24][CH3:25])=[CH:16][C:15]=1[CH2:14][CH2:13]3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 131725387HCID 131725387, compound

Product 1

HCID 86594473HCID 86594473, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 59.9 mg (0.155 mmol) of 55, 269 μL (1.55 mmol) of iPrEt2N, 118 μL (1.55 mmol) of MOMCl in anhydrous toluene (2 mL) was stirred at rt for 22 h. The reaction mixture was poured into H2O (70 mL) and extracted with CH2Cl2 (3×, 50 mL). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo giving a yellow oil. Purification by flash chromatography on a 2×17 cm column of silica gel using 3:1 hexanes/EtOAc as eluent gave 53.7 mg (80%) of 56. Data for 56: TLC, T-2, Rf 0.8; 1H NMR (500 MHz, CDCl3) δ 0.85 (s, 3H, H-18), 1.29 (t, 3H, J=7.2 Hz, CH2CH3), 3.37 (s, 3H, —CH2OCH3), 3.77 (t, 1H, J=8.7 Hz, H-17α), 3.78 (s, 3H, ArOCH3), 4.20–4.14 (m, 2H, —CH2CH3), 4.66 (s, 2H, OCH2O), 6.61 (d, 1H, J=2.8 Hz, H-4), 6.71 (dd, 1H, J=8.8, 2.8 Hz, H-2), 7.21 (d, 1H, J=8.8 Hz, H-1).

Workup

  1. extractionextracted with CH2Cl2 (3×, 50 mL)
  2. dry with materialCombined organic extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customgiving a yellow oil
  5. customPurification by flash chromatography on a 2×17 cm column of silica gel using 3:1 hexanes/EtOAc as eluent

Sources & evidence

ORD record
ord-170640333a4247778e70e7dd7ad2c48d
Source dataset
uspto-grants-2006_03
Patent number
US07015211B2

Reaction notes

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