Sodium Hydroxide → HCID 58226384, compound

HRID 1614854Notes

Reaction equation

HRID 1614854 reaction equation
[CH3:1][O:2][CH:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:4][C@@H:5]1[O:8][C:7](=[O:9])[CH2:6]1.[OH-:19].[Na+]>C1COCC1.O>[OH:8][C@@H:5]([CH2:4][CH:3]([O:2][CH3:1])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:6][C:7]([OH:19])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58226382HCID 58226382, compound

Product 1

HCID 58226384HCID 58226384, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7 (187 mg, 0.729 mmol, 1.0 equiv) in THF (2.5 mL) was added a solution of NaOH (32.) mg, 0.802 mmol, 1.1 equiv) in water (1 L). The reaction mixture was stirred at rt for 2 h, transferred to a separatory funnel, diluted with water (5 mL) and extracted with ether. The aqueous layer was acidified with 2 N HCl (3 mL) and extracted with ether (2×15 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford (3S)-1 (187 mg, 93%) as a colorless oil that was used without further purification: ATR/IR 2920, 2851, 1709, 1412, 1189, 1079, 738 cm−1; 1H NMR (CDCl3) 4.85-4.7 (m, 1H), 3.55-3.45 (m, 1H), 3.39, 3.38 (2s, 3H), 2.56-2.52 (m, 2H), 1.80-1.35 (m, 3H), 1.35-1.25 (m, 14H), 0.90 (t, 3H, J=6.9 Hz); 13C NMR (CDCl3) 176.5, 175.8, 81.5, 78.7, 68.0, 65.3, 56.7, 55.9, 41.5, 39.6, 39.0, 32.8, 32.6, 31.8, 29.7, 29.5, 29.2, 25.1, 24.4, 22.6, 14.1; MS (EI) m/z 274 (M+, 0.5), 256 (0.5), 171, 25, 129 (100), 97 (15).

Workup

  1. customtransferred to a separatory funnel
  2. extractionextracted with ether
  3. extractionextracted with ether (2×15 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto afford (3S)-1 (187 mg, 93%) as a colorless oil that
  7. customwas used without further purification

Sources & evidence

ORD record
ord-29c60e4d7ee44fd2beaa7c146a11494b
Source dataset
uspto-grants-2014_07
Patent number
US08765431B2

Reaction notes

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