Sodium Methoxide → HCID 58681695, compound

HRID 2059564Notes

Reaction equation

HRID 2059564 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[CH2:4][O:5][CH2:6][C@H:7]1[O:11][CH:10]([O:12][CH3:13])[C@H:9](CC([O-])=O)[C@H:8]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27].C[O-:34].[Na+]>CO>[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[CH2:4][O:5][CH2:6][C@H:7]1[O:11][CH:10]([O:12][CH3:13])[C@H:9]([OH:34])[C@@H:8]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86642241HCID 86642241, compound

Product 1

HCID 58681695HCID 58681695, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

To (3R,4R,5R)-5-(2,4-dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-acetate (10 g, 19.1 mmol) in MeOH (150 ml) is added a solution of 30% NaOMe in MeOH (5.37 ml, 28.6 mmol) and the reaction is stirred at 20° C. for 30 mins. The reaction mixture is concentrated and dissolved in IPAC (100 ml), washed with 1 N HCl solution (50 mL) and water (50 mL) and concentrated to give (3R,4S,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-ol as a yellowish oil. The obtained crude compound is used for the next step without further purification. 1H-NMR (CDCl3, 400 MHz): δ 7.43 (d, J=8.1 Hz, 1H), 7.35-7.31 (m, 3H), 7.23 (dd, J=2.1, 4.0 Hz, 1H), 7.21-7.10 (dd, J=2.1, 4.0 Hz, 1H), 4.92 (d, J=4.6 Hz 1H), 4.77 (d, J=13.4 Hz, 1H), 4.68 (d, J=13.4 Hz, 1H); 4.60 (d, J=13.0 Hz, 1H), 4.56 (d, J=13.0 Hz, 1H), 4.25 (q, J=4.0 Hz, 1H), 4.19 (dd, J=6.8, 4.8 Hz, 1H) 3.86 (dd J=6.9, 7.0 Hz 1H), 3.60 (d, J=10.5 Hz, 2H), 3.48 (s, 3H); 13C-NMR (CDCl3, 100 MHz): δ 134.2, 134.1, 133.9, 133.5, 133.4, 129.9, 129.8, 129.1, 129.08, 127.11, 127.08, 102.8, 81.6, 77.4, 72.0, 70.8, 70.0, 69.5, 55.6 (one carbon overlapped); ESI-MS: calcd. for C20H20Cl4O5 (M+NH4+, 480.0). found: 498.0.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutiondissolved in IPAC (100 ml)
  3. washwashed with 1 N HCl solution (50 mL) and water (50 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b9f7a85b920b436d8744c440dbe238c2
Source dataset
uspto-grants-2012_10
Patent number
US08278282B2

Reaction notes

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