Water → HCID 11144234, compound

HRID 1744221Notes

Reaction equation

HRID 1744221 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][C@@H:16]4[CH:28](C(O)=O)[C:29]([OH:31])=[O:30])[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>COCCOCCOC>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][C@@H:16]4[CH2:28][C:29]([OH:31])=[O:30])[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 11730256HCID 11730256, compound

Product 1

HCID 11144234HCID 11144234, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
162 °C

Procedure

A solution of 297 mg (0.642 mmol) of 62 crude in 10 mL of 2-methoxyethyl ether was stirred and heated at 162° C. for 15 min. The reaction mixture was allowed to cool to rt, poured into H2O (100 mL) and extracted with EtOAc (3×, 70 mL). Combined organic extracts were washed with 10% Na2S2O5 and concentrated in vacuo giving a yellow oil which was used without purification in the next step. Data for 63: TLC, T-3, Rf 0.58; 1H NMR (400 MHz, CDCl3) δ 1.01 (s, 3H, H-18), 5.04 (s, 2H, benzylic-H), 6.72 (d, 1H, J=2.6 Hz, H-4), 6.81 (dd, 1H, J=8.5, 2.6 Hz, H-2), 7.22 (d, 1H, J=8.5 Hz, H-1), 7.30–7.45 (m, 5H, Ar—H).

Workup

  1. temperatureto cool to rt
  2. extractionextracted with EtOAc (3×, 70 mL)
  3. washCombined organic extracts were washed with 10% Na2S2O5
  4. concentrationconcentrated in vacuo
  5. customgiving a yellow oil which
  6. customwas used without purification in the next step

Sources & evidence

ORD record
ord-daf55640446e46cbbbcf91462d3f622b
Source dataset
uspto-grants-2006_03
Patent number
US07015211B2

Reaction notes

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