Sodium hydride → HCID 70465682, compound

HRID 1284876Notes

Reaction equation

HRID 1284876 reaction equation
[CH2:1]([O:3][C:4](=[O:44])[CH:5]([CH2:11][C:12]([F:43])([F:42])[CH2:13][C@H:14]([C@@H:16]1[C@:33]2([CH3:34])[C@H:19]([C@H:20]3[C@H:30]([CH2:31][CH2:32]2)[C@:28]2([CH3:29])[C:23]([CH2:24][C@@H:25]([O:35][CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][O:37]4)[CH2:26][CH2:27]2)=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)[CH3:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].[Cl:47]N1C(=O)CCC1=O>C(COC)OC>[CH2:1]([O:3][C:4](=[O:44])[C:5]([Cl:47])([CH2:11][C:12]([F:42])([F:43])[CH2:13][C@H:14]([C@@H:16]1[C@:33]2([CH3:34])[C@H:19]([C@H:20]3[C@H:30]([CH2:31][CH2:32]2)[C@:28]2([CH3:29])[C:23]([CH2:24][C@@H:25]([O:35][CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][O:37]4)[CH2:26][CH2:27]2)=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)[CH3:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31398ChlorosuccinimideHCID 57222703HCID 57222703, compound

Product 1

HCID 70465682HCID 70465682, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The diester (9) (700 mg, 1.125 mmol) was treated with sodium hydride (39 mg, 1.625 mmol) in dimethoxyethane (20 ml) at room temperature under argon atmosphere for 1 hr. Then, to this solution N-chlorosuccinimide (180 mg, 1.35 mmol) was added and the mixture was stirred at room temperature for 1 hr. The usual work-up (ether for extraction) gave a crude product, which was applied to a column of silica gel (20 g). Elution with n-hexane-ether (10:1) provided tthe chlorodiester (10) (730 mg, 99%), glass. 1H-NMR: 0.72 (3H, s, 18-H3), 1.02 (3H, s, 19-H3), 1.10 (3H, d, J=6 Hz, 21-H3), 1.30 (6H, t, J=7.5 Hz, --CO2CH2CH3), 2.95 (2H, t, J=15 Hz, 24-H2), 3.52 (2H, m, THP), 3.88 (1H, m, 3-H), 4.32 (4H, q, J=7.5 Hz, --CO2CO2CH3), 4.72 (1H, m. THP), 5.38 (1H, m, 6-H). MS m/z: 554, 520.

Workup

  1. extractionThe usual work-up (ether for extraction)
  2. customgave a crude product, which
  3. washElution with n-hexane-ether (10:1)

Sources & evidence

ORD record
ord-720094d5d0254fe4bac473835d30abef
Source dataset
uspto-grants-1986_01
Patent number
US04564474

Reaction notes

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