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Water → (4R,4aS,7R,7aR)-4-[(1R)-1,2-dihydroxyethyl]-7-ethoxy-2,2-dimethyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one

HRID 1670441
Notes
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Reaction equation

HRID 1670441 reaction equation
CC1(C)[O:6][C@@H:5]([C@H:7]2[O:12][C:11]([CH3:14])([CH3:13])[O:10][C@H:9]3[C@@H:15]([O:19][CH2:20][CH3:21])[C:16](=[O:18])[O:17][C@@H:8]23)[CH2:4][O:3]1.O>C(O)(=O)C>[OH:6][C@@H:5]([C@H:7]1[O:12][C:11]([CH3:14])([CH3:13])[O:10][C@H:9]2[C@@H:15]([O:19][CH2:20][CH3:21])[C:16](=[O:18])[O:17][C@@H:8]12)[CH2:4][OH:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 962WaterHCID 67329262(4R,4aS,7R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-7-ethoxy-2,2-dimethyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one

Product 1

HCID 67328965(4R,4aS,7R,7aR)-4-[(1R)-1,2-dihydroxyethyl]-7-ethoxy-2,2-dimethyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-oneYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.62 g of 48 (8.28 mmol) are introduced into a 100 mL three-necked flask containing 16 mL of water and 16 mL of acetic acid. The medium is stirred for 24 h at RT and then the reaction medium is concentrated under vacuum. The residues are disintegrated with 25 mL of isopropyl ether, filtered and dried under vacuum. 2.15 g of expected product 49 (white solid) are obtained.

Workup

  1. concentrationthe reaction medium is concentrated under vacuum
  2. filtrationfiltered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4800204efc744f58af7e51e840e5a0eb
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07994161B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes